Hi there,
Thanks in advance for reading my post and providing your opinion. This one is driving me nuts!
I'm sitting on about $200k of my former employer's (Paypal) company stock (1/3 of investments). Estimated Long-term Capital Gains Tax is $12k.
I'm debating if I should sell right away (to avoid Concentration Risk) or wait for a year or two until I plan to retire (and have less enough income so can most likely avoid this tax).
Ah, my guess was right: $12k / 0.15 = $80k, from your thread about selling or not. Taxes are a separate issue, so I think it's fair to have 2 threads.
Every year, single filers have $40k of room for 0% long-term capital gains (LTCG). But that's misleading, since LTCG start on top of your other income/dividends. For example, if you have $15k of dividends, you only have ($40k - $15k) = $25k at 0% LTCG tax rate. Married filers get $80k at 0%.
Your W-2 income goes away when you stop working. But you will probably still have any 1099-DIV and 1099-INT after you retire. You might want to add those up, so you can estimate how much you can sell each year without incurring tax.