The Cosmic Avenger
Thinks s/he gets paid by the post
I finally opened a donor-advised fund this year, and my current strategy is to donate all appreciated stock. I inherited some stock and funds that have appreciated a fair amount, and I might as well save us the capital gains tax. Other than this strategy, I wasn't planning on changing our charitable giving. Let's say for the sake of this discussion we give about $10K a year, to a few dozen charities. So my plan is to put $10K of appreciated stock into the DAF, then repurchase that stock, thus resetting our cost basis. We're spending $10K out of checking, basically, to purchase that stock when otherwise we'd be using it for charitable giving, so that's a wash.
Now, I see the advantages of bunching, especially with the new standard deduction. However, my plan to repurchase stock doesn't work with bunching, as we set aside $10K per year for charitable giving, so that extra $20K in stock would not be repurchased right away.
Should I just bunch next year, and spread the $30K stock repurchase over 3 years? These are steady, large cap stocks that will probably be more expensive in years 2 and 3, and that grates on me. I feel like I might lose more than I would gain in tax savings by bunching. And as we know, there's no way to reliably estimate a stock's appreciation or everyone would be able to guarantee returns! Should I review the last three years performance for the stocks in question and see how I would have made out if I had bunched 3 years ago? That seems....irrelevant.
So, do you all think bunching is a good strategy or not if my overall strategy is to keep my taxable investments and reset their cost basis?
Now, I see the advantages of bunching, especially with the new standard deduction. However, my plan to repurchase stock doesn't work with bunching, as we set aside $10K per year for charitable giving, so that extra $20K in stock would not be repurchased right away.
Should I just bunch next year, and spread the $30K stock repurchase over 3 years? These are steady, large cap stocks that will probably be more expensive in years 2 and 3, and that grates on me. I feel like I might lose more than I would gain in tax savings by bunching. And as we know, there's no way to reliably estimate a stock's appreciation or everyone would be able to guarantee returns! Should I review the last three years performance for the stocks in question and see how I would have made out if I had bunched 3 years ago? That seems....irrelevant.
So, do you all think bunching is a good strategy or not if my overall strategy is to keep my taxable investments and reset their cost basis?