DAF Timing Question

[Much Fishing to Do]

I suspect I'm going to be in a much higher tax bracket this year than following years so intend to make a large contribution of appreciated securities to a Donor Advised Fund I set up last year and then use this fund to make my charitable contributions from throughout retirement.  Does it make the most sense for me to wait and do this at the end of the year?  It seems straight forward that if 1) I assume I'm no market timing expert and stocks generally go up over time and 2) I will not have to pay capital gains on this and 3) I will get the deduction of the amount the securites are worth when I make the contribution, then it makes the most sense for me to do this as late as possible in the year as on average that will likely increase the amount of my eventual deduction.  Any flaw in this reasoning?

[ISawTheLight]

The only comments I would make: 

1)  If you plan on making charitable contributions this year, you should probably fund early enough to do those contributions from the DAF.  (Since you set up a DAF last year, maybe there's already enough in there to fund your 2018 donations.  That's not apparent from your original post.)
2)  If you're donating mutual funds, be sure to send them off before they issue their 2018 distributions at year end.

[MustacheAndaHalf]

If you time it too close to December 31st, you might incur delays that push it past the end of the year.  I seem to recall it can involve a Medallion guarantee which requires a visit in person.

The stock market won't necessarily act in whatever manner is prescribed for it.  That being said, if you wait until Dec and the markets drop, know that in general you had the right idea.  The stock market's value does tend to go up over time.

[seattlecyclone]

I started my Vanguard DAF last year around mid-December. That was just soon enough to get some funds transferred in from Vanguard (takes longer from other places) and make a few distributions to charities by the end of the year. I'd probably recommend getting the process going by December 1 just to be on the safe side.

[CoffeeAndDonuts]

You said you "suspect" you'll be in a higher bracket.

As long as it's suspect, I'd defer action until the clock is closer to running out.

Here's how I'd approach it:
1. Establish daf with provider that you have a brokerage acct with if that's reasonable at all.
2. Perhaps do the minimum (e.g. $5k at Schwab) right away if you'll be giving that regardless.
3. Alternatively, defer giving until daf/tax questions are figured out more clearly or clock is an issue.
4. Stay in market. If stocks decline, maybe you'll have some deductible losses and would have donated less. But as you note, they're more likely to rise in which case your deduction grows.
5. Research this fully... From paperwork to taxes. Don't forget limits on deductions to charity. https://www.irs.gov/charities-non-profits/charitable-organizations/charitable-contribution-deductions

With regard to timing, my initial establishment of a daf with Schwab was a few years ago and just $5k cash. I think that was mid December. Last year I transferred assets from Merrill edge brokerage to schwab in early December, then did Schwab brokerage to Schwab daf around perhaps Dec 27 or so. Worked fine and Schwab's dates were clear on advance.

Congrats on a good year and on making giving a priority. We're catching up after not giving much in our 20s and most of 30s.

[Much Fishing to Do]

Thanks Everyone. 

That's a really good point Isawthelight about donating before year-end distributions (it'll likely come from a small cap mutual fund that has appreciated a ton in the last ten years), I didn't think of that one though it looks like that occurs Dec 27 and I wouldn't try to cut it that close anyway given how clumsy a transaction it is.

I think I'll just pick Dec 1 to ensure there is plenty of time.  Thats a good point CoffeeandDOnuts re: waiting to see if it is a higher bracket year, which is always another good benefit of waiting as you better know your position, though its already clear I'll be in the highest bracket this year so my guessing is re: future years me not being in this bracket (particularly good business year this year but I'm toast and downshifting now)