I'd like to start giving more to charity. As more of my assets are in the form of equities, it would be easier for me to donate shares instead of cash. Though I'd like to do this in a way that cuts down on the complexity for charities handling the donation. Ideally I'd like the charities to just get cash in the form of a check than try to deal with transferring some shares from my brokerage to there's (assuming that is even an option as it might not be with smaller, local charities). While I could sell the shares and donate cash, this would trigger a tax, which either would eat into the donation or would put me in the situation of covering this tax with other funds. So would prefer to donate the shares directly somehow (without having to sell them myself) that wouldn't burden the charity (they still receive cash).
While not the goal of charity, it would be nice if I could receive the itemized deduction when I donate. Since I don't otherwise itemize (rent so no mortgage, no state income tax, etc.), it makes more sense to do a larger donation in one year (possibly covering donations for a few years); however, it may be better for charities to have some consistent cashflow to plan around (receiving donations annually, quarterly, or perhaps even monthly). As this can prove logistically challenging when combined with the donations of shares, trying to meet the requirements before the end of the tax year, and having good records both for myself and when the IRS inevitably inquires about these lumpy donations over the years, some sort of vehicle to help manage these donations seems quite helpful.
After thinking about these constraints and reading up here and elsewhere, it seems like a Donor Advised Fund (DAF) would fit these needs perfectly. Namely I can front load a few years of donations pretty easily. The DAF then tracks this information for reporting purposes. Within the DAF, I can transition from a more aggressive investment style I have for myself to a more conservative one to help preserve the funds as they get doled out to charities over the years. Finally the DAF can just send checks to the charities keeping things simple for them to receive.
If it's relevant my portfolio can be seen here ( viewtopic.php?p=5591362#p5591362 ), though I'm guessing it doesn't matter much for this question. What probably is important is the shares that I would like to donate are either at Vanguard in the form of Vanguard mutual funds or at Schwab in the form of individual shares in form of ESPP and RSU.
Given this, I have some questions:
1. Does my understanding of DAFs seem correct or am I missing things?
2. Is using a DAF for this purpose reasonable? Or are there other reasonable options I'm missing?
3. Where would be a good place to setup this DAF and why? (FWIW I have accounts with Fidelity, Schwab, and Vanguard, which all seem to offer this)
4. If transferring shares between brokerages is involved, how difficult is this? (I suppose having multiple DAFs could avoid this, but would prefer to just have one to keep things easy to manage)
5. Also has one had experience doing this with ESPP or RSU shares? Anything to be aware of in this case?
6. Anything else I might be missing?
Thanks in advance for your thoughts and feedback!
