I did not know what NAC was -
https://www.goodhousekeeping.com/health/diet-nutrition/a44591291/nac-supplement-benefits/

Well, with either #1 or #2, you get the tax saving, but have $40 in your hands and still have $24 to soft-manage within the DAF.
Remember, $64K with large unrealized gain does have higher market risk.
Actually, a 3rd scenario (variation of #2) can be constructed so that you donate some in-kind to DAF and cash the remainder so that the net tax impact is zero. And you end up with the combo of cash in your hands plus a good chunk in DAF to soft-manage.
Money in the DAF is out of your estate.
There are also income limitations for DAF contributions,
"Overall deductions for donations to donor-advised funds are generally limited to 50% of your adjusted gross income (AGI). The limit increases to 60% of AGI for cash gifts, while the limit on donating appreciated non-cash assets held more than one year is 30% of AGI. The IRS permits a carryover for five tax years, should your charitable deduction exceed AGI limits in a given tax year."
https://www.schwabcharitable.org/non-cash-assets/publicly-traded-securities

Book gains and fund DAF with those gains
I'm confused about what you mean by "book gains". Also, it doesn't look like net effect on taxes comes out to zero.
I'll make this concrete. $40K cost for stock, $64K present value, 15%/22% tax bracket (cap gains/ord. income).
Scenario 1: Liquidate all, donate $24K gain ($24K deduction)
cap gains tax = 15% x $24K = $3.6K
ordinary tax savings = 22% x $24K = $5.28K
net tax = -$1.68K
Scenario 2: Donate $24K gain in kind, liquidate rest ($40K)
cap gains tax = 15% x 40/64 x $24K = $2.25K (less because you don't sell all)
ordinary tax savings = 22% x $24K = $5.28K
net tax = -$3.03K
Donating securities directly usually comes out better than selling and donating proceeds. The tax savings above assume that one gets the full benefit of itemizing the contribution.
One benefits (gets a higher deduction) only to the extent that itemized deductions exceed the standard deduction. So if a $10K contribution pushes itemized deductions just $4K over the std deduction amount, one gets only $4K in increased deductions, not the full $10K.
As you noted, the trick is to bundle deductions. That way, instead of losing some deduction value in reaching the std deduction amount each year, one reaches the threshold this year and then keeps adding. DAFs are an excellent vehicle to do this.

”The Psychology of Trafing Trading is a good book I read many moons ago which I recommend to people who want to understand emotional techniques to deal with trading. This is not the same as investing for which you are better off listening to munger interviews.”

Right. Trading can be highly profitable as many here demonstrate. As @Equalizer noted, riskier holdings lend themselves to smaller commitment. So the perceived prize from any single holding is probably less than one might expect. Yet the mental work (anguish?) is very intense compared to owning a diversified fund.
The ‘07-‘09 fiasco was relatively short in comparison to some of the major historical market slides. May have taught some of us the wrong lesson.
I’d suggest following at least three different market commentators (pundits) with contrasting market outlooks or approaches to investing, including one bearish source. Try to give each some credence and then chart your course..
The portfolio analyzers may help keep one (ie he, she, it, they, them) on an even knell. If it’s hard to find compelling buys, ratchet up the cash, bond, “other” or income focused part while pulling back a bit on the percentage in stocks. Personally, I reached a high of 48-50% equities 12-18 months ago. Has fallen to 35% today. My unorthodox approach is to swap-out entire portfolio segments (each representing about 17%).Hence, the considerable slug in LCORX (60+% equity) was recently moved into LPXAX which invests primally in short duration bonds and preferred stocks. A year from now, who knows? Might sell it and move back into a more aggressive holding if market valuations change. (My positioning is for a 78 year old and not a recommendation for others.)
I do not recommend alcohol for any important thought activity like trading. But it probably works for some. I began taking small doses of NAC, a non-prescription health supplement a decade ago after reading a WSJ piece saying it may stop nail biting. And it worked after 40+ years of gnawing. Works by reducing compulsive tendencies. I don’t think it affects my investing. But possibly makes the bumps along the way easier to tolerate.

@equalizer, will you be covered through employer group health insurance plan until 65 when Medicare kicks in?
Years ago, mine did only IF I opted for pension, not lump-sum. But plans differ on this.

I’m taking “early” retirement next week at 57, so been thinking about risk/reward. Have coworkers who couldn’t tell you what WSJ means, but had retirement 100% in SPY for 30 plus years. Compared to 70/30 ratio, could mean 8% AR vs 11%. Over 33 years
, could mean at least one million more. Coulda had the brokers yacht and Ferris Bueler’s Ferrari…gonna drink my big Black Cow…
One of the Ferraris From Ferris Bueller's Day Off Just Sold for $396,000 in 2020. Replica 250 GT.

Yikes. UVXY's been really Ultra the last 4 years: -88%, -45%, -88%, -54% ytd.

Vix started year ar 13 and is ending near 14. This ETF is probably one of the worst ETFs ever designed if you want to make money.

”Stocks Could Gain Another 20% in 2025. Embrace the Bubble.”
This week’s Barron’s cover story (also linked/ referenced by @Stillers above)
Here’s the cover art. Maybe title it “Going, Going, Gone!” ?

Didn't like long bonds. Doesn't think next year will be good (as the last 2 years) or bad for stocks as too many variables like tariffs, immigration etc... maybe 15%. Stay on the short side of the yield curve. I don't remember most of it either even though I just watched it. He pushed his ETF BINC with has a pretty good quality bonds but it's only been around since 5/2023. I compared it to RCTIX and PIMIX, it fits in between them but I like RCTIX better.

David G is calling we are in a bubble territory for equities not seen during his career. Evidently, PRWCX is 5% underweight at 56% equities. I am guessing it has to do with the higher discount rate. May be he is betting 10 yr interest rates to stay higher.
Rick Rieder, blackrock, manages a huge amount of allocation assets. Let us find his latest musings about the market, rather than go just with David G’s rockstar status.

Dec 12th Episode

Warren Pierson, Co-Chief Investment Officer of Baird Advisors and portfolio manager of the top-rated Baird Aggregate Bond Fund, explains the newfound popularity of bonds.

Dec 14th Episode:

Great investor David Giroux has cut way back on stocks and increased bonds in his top performing T. Rowe Price Capital Appreciation Fund. He explains why stock prices are scary and bonds look better than most stocks in 2025.

So, what are the bond kids thinking??? A .25 rate cut this coming week and then FINI for a length of time due to inflation. Perhaps there is concern with required skillsets for proper restructuring of multiple departments within the U.S. government by questionable managers, that will be forthcoming in a few weeks and retaliation for proposed tariffs. The Ontario, Canada Premiere has issued a 'Ya wanna play to DJT & Co.'. Perhaps there is overall concern with what comes after January 20, 2025.
NOTE:

My intention, at this time; is to present the data for the selected bond sectors, as listed; through the end of the year (2024). This 'end date' will take us through the U.S. elections period, pending actions/legislation dependent upon the election results, pending Federal Reserve actions and market movers trying to 'guess' future directions of the U.S. economy. As important during this period, are any number of global circumstances that may take a path that is not expected; and/or 'new' circumstances. In the 'cooking pot' we currently have the big ingredients of the middle east and also, how much damage Ukraine may inflict upon Russia and the response.

FIRST: NOTHING TO ADD/ALTER regarding 'Never-Never Land'. The pre-DC world shift of January, 2025 remains 'interesting' at this time! We're in a 'Never-Never Land' (events you never imagined) of potential large impacts upon various economic functions emanating from a central government in the coming months and years. What comes next for the investing world of bonds is not yet known or fully understood, except for those have a better guessing system than I. I can only watch and listen a little bit and let the numbers try to bring forth meaningful directions.
W/E December 13 , 2024. Bond NAV's PINCH your nose, avoid the SMELL
--- 'Course, all the bond sectors in the list find their reasons for price movements, and we find most bond sectors HAD THE BIG HEAD SLAP for this week's pricing. The majority of bond sectors were down all day, each day of the week. All durations pricing were down every day of the week. So, depending on where you're 'hanging' your bond market monies, the pricing this week, was NASTY AND DOWN. The MINT etf, to the best of my recall, has maintained a positive price for the year, each and every week; and this remains for this week.
A few numbers for your viewing pleasure.
NEXT:
*** UST yields chart, 6 month - 30 year. This chart is active and will display a 6 month time frame going forward to a future date. Place/hover the mouse pointer anywhere on a line to display the date and yield for that date. The percent to the right side is the percentage change in the yield from the chart beginning date for a particular item. You may also 'right click' on the 126 days at the chart bottom to change a 'time frame' from a drop down menu. Hopefully, the line graph also lets you view the 'yield curve' in a different fashion, for the longer duration issues, at this time. Save the page to your own device for future reference. NOTE: take a peek at the right side of this graph to find the yield swings of the past week, and for the current yields for the last business day.
For the WEEK/YTD, NAV price changes, December 9 - December 13, 2024
***** This week (Friday), FZDXX, MM yield continues to move with Fed funds/repo/SOFR rates; and ended the week at 4.44% yield (Unchanged for the week). Fidelity's MM's continue to maintain decent yields, as is presumed with other vendors similar MM's. Theoretically, a new yield bottom is in place, until the next FED action. SO, one is still obtaining a decent MM yield. MOST MM's found a .00% basis change in yield for the week. MM's yields were unchanged, for the week.................
--- AGG = -1.42% / +2.04% (I-Shares Core bond), a benchmark, (AAA-BBB holdings)
--- MINT = +.07% / +5.68% (PIMCO Enhanced short maturity, AAA-BBB rated)
--- SHY = -.17% / +3.70 % (UST 1-3 yr bills)
--- IEI = -.84% / +2.09% (UST 3-7 yr notes/bonds)
--- IEF = -1.66% / +.36% (UST 7-10 yr bonds)
--- TIP = -.96% / +2.67% (UST Tips, 3-10 yrs duration, some 20+ yr duration)
--- VTIP = -.12% / +4.89% (Vanguard Short-Term Infl-Prot Secs ETF)
--- STPZ = -.25% / +4.53% (UST, short duration TIPs bonds, PIMCO)
--- LTPZ = -3.25% / -2.12% (UST, long duration TIPs bonds, PIMCO)
--- TLT = -4.49% / -5.46% (I Shares 20+ Yr UST Bond
--- EDV = -6.41% / -9.45% (UST Vanguard extended duration bonds)
--- ZROZ = -7.33% / -12.09% (UST., AAA, long duration zero coupon bonds, PIMCO
--- TBT = +9.59% / +20.30% (ProShares UltraShort 20+ Year Treasury (about 23 holdings)
--- TMF = -12.62% / -29.52% (Direxion Daily 20+ Yr Trsy Bull 3X ETF (about a 2x version of EDV etf)
*** Additional important bond sectors, for reference:
--- BAGIX = -1.31% / +2.68% Baird Aggregate Bond Fund (active managed, plain vanilla, high quality bond fund)
--- USFR = +.10% / +5.19% (WisdomTree Floating Rate Treasury)
--- LQD = -1.79% / +2.26% (I Shares IG, corp. bonds)
--- MBB = -1.54% / +1.89% (I-Shares Mortgage Backed Bonds)
--- BKLN = +.14% / +8.10% (Invesco Senior Loan, Corp. rated BB & lower)
--- HYG = -.61% / +8.44 % (I Shares High Yield bonds, proxy ETF)
--- HYD = -1.23%/+4.96% (VanEck HY Muni)
--- MUB = -1.20% /+1.68% (I Shares, National Muni Bond)
--- EMB = -1.47%/+7.15% (I Shares, USD, Emerging Markets Bond)
--- CWB = -.95% / +14.05% (SPDR Bloomberg Convertible Securities)
--- PFF = -1.35% / +8.92% (I Shares, Preferred & Income Securities)
--- FZDXX = 4.44% yield (7 day), Fidelity Premium MM fund
*** FZDXX yield was .11%, April,2022. (For reference to current date)
Comments and corrections, please.
Remain curious,
Catch

12/13/2024. Dani Burger is in.
https://www.bloomberg.com/news/videos/2024-12-13/bloomberg-real-yield-12-13-2024-video
The Market is virtually certain of a .25% rate cut this month from The Fed.
Rick Rieder: back end of the curve is not worth it. Expect volatility.
Do we get a cut, and, as has been the case, do yields keep going HIGHER? The front end should stay put, or "pegged." The long end will be range-bound in the 1st quarter of '25, perhaps up to 4.5%.
"Fiscal adventurism" coming next year. Watch for the prospect of pressure on the labor force if deportations get going. The WORD will be uncertainty.... What about overseas developed bonds? Europe, especially: fiscal expansionism won't be "the story." Austerity to any degree is the opposite of what we should expect HERE. Currency hedge with Gilts and in Japan are relatively attractive.
Past week was 2nd-busiest of the year with credit issuance. TD (fresh off a not very old news story about it being lax to prevent money laundering---) was one of the "leaders." Tighter spreads will continue and be even more pronounced. Triple-Cs GAINED for a 4th week. Credit spreads are at a 3-year low.

The Week in Charts (12/13/24)
The most important charts and themes in markets and investing, including:
00:00 Intro
00:40 Topics
01:41 Inflation Is Warming
05:44 Free Wealth Path Analysis
07:48 Easing Into a Mania
19:27 Is Free Money the Cure For High Prices?
27:20 Nasdaq 20,000
29:19 Apple's Highest Valuation Ever
38:42 America's Exceptional Valuation
47:32 Rising Real Wages and Spike in Small Business Optimism
Video
Blog

@MikeM: On a hunch, just the other day, I did the same with VEEV, which I had been watching. Damned if it didn't shoot up at the opening the next day. I put in a sell order, Schwab improved it by $2, and I had a $500 profit. I used it all to make donations to local public radio, MFO, and a couple of other causes. Believe me, it is truly rare for me to succeed in that way.

msf, here is the key statement from my Original Thread Post regarding CDs that are maturing:
"I am wrestling with renewing at the 4.3% rate, with almost no stress, or jumping back into the more active investing options. Anyone else in a similar situation?
If you are a CD investor, with current CDs that are maturing, I would be interested in your response regarding your personal investing decision, about reinvesting the maturity back into CDs, or shifting to a different kind of investment.

In one sense I'm not in a similar situation. I've been taking advantage of the inverted yield curve we've had for a few years and so I do not have bonds or CDs maturing soon. OTOH, I'm in a similar situation because I have this short term cash that has been giving me better returns but is no longer doing so.
The return to a non-inverted yield curve was due to short term rates dropping faster than long term rates, not because long term rates rose. See M* graph here of curves for 2020 (ZIRP), Sept 2023 (highest, inverted), June 2024 (similar shape with a bit lower yield), and Sept 2024 (flat-ish, 2/3% lower, greater drop at short end)
https://www.morningstar.co.uk/uk/news/255673/how-to-position-your-bond-portfolio-as-short-term-yields-fall.aspx
That piece was written three months ago and M* was suggesting finally going longer (i.e. intermediate as opposed to short). I stayed short - too much uncertainty and now with "promised" tariffs, migrant expulsions (affecting labor costs), etc., rising inflation (and rising interest rates) seem far from improbable. Just the other day I heard that it will be hard to bring down food prices. Quelle surprise.
That Sept. M* piece was written almost exactly at a minimum in 10 year Treasury rates: 3.63% on Sept 16th, currently 4.32%. A purchase of a multi-year CD or Treasury bond in Sept would have locked in a lower rate than one should be able to get now.
https://home.treasury.gov/resource-center/data-chart-center/interest-rates/TextView?type=daily_treasury_yield_curve&field_tdr_date_value=2024
Cash (1-2 month maturity) is still looking good and I see no reason to gamble before Feb 2025 on the direction of rate movements.
I've given my thoughts before on places to keep cash short term. If you can get into a low cost Treasury MMF (Treas only for high income tax states), they are yielding near or more than prime MMFs (and more after-tax). Those are typically $1M min: SUTXX (4.43% SEC yield, 4.53% APY), FSIXX (4.44% SEC yield, 4.54% APY) w/$1 min at Merrill Edge. Going out a bit longer is RPHIX. Slightly longer still are AAA CLOs like PAAA (pure AAA) and JAAA (smidgen of AAs, longer history).
JAAA acquitted itself respectfully in 2022, dropping 2.33% from Jan 1 before recovering. In comparison, floating rate ETFs like FLRN and FLOT dropped 1.34% and 1.65% respectively. They all were positive for the year, while MINT bottomed out at -2.16% from Jan 1 and lost a percent on the year.

Soon maybe the Bored Ape NFT's will be back. Sold for millions now worth 50-70k if you can even figure it out. A 90% decline since mid 2022 from what I can find. OUCH!! I'll waste spend my money on cars, women and beer.

I accidentally snorted out whisky at reading half of these ... I was only trying to find the quote that no one has yet devised, concocted, imagined, or plausibly advocated a use case
https://www.cryptoaltruism.org/blog/15-quotes-about-the-potential-of-blockchain-and-crypto
efficiency! math!
andreesen sounds like he is talking about full-faith / -credit currency

Unbelievable set of quotes (are they real?) Well, all I can say is:
Song: Happy Days Are Here Again
Lyrics: Jack Yellen(1) (4) (5)
Music: Milton Ager(2) (4) (5)
Year: 1929(3) (5)
Genre: Popular
Country: USA
Happy days are here again!
The skies above are clear again,
Let us sing a song of cheer again,
Happy days are here again!
Altogether shout it now,
There's no one who can doubt it now,
Let us tell the world about it now,
Happy days are here again!
Your cares and troubles are gone
There'll be no more from now on!
This song was originally posted on protestsonglyrics.net
Happy days are here again!
The skies above are clear again
Let us sing a song of cheer again
Happy days are here again!
So long sad times, go long bad times,
We are rid of you at last;
Howdy gay times, cloudy gray times
You are now a thing of the past.
Happy days are here again!
The skies above are clear again
Let us sing a song of cheer again
Happy days are here again!
This song was originally posted on protestsonglyrics.net
Your cares and troubles are gone
There'll be no more from now on!
Happy days are here again!
The skies above are clear again
Let us sing a song of cheer again
Happy days are here again!
Happy Days are Here Again Lyrics