Last year I needed to raise a large amount of cash for a house down payment and sold appreciated shares across accounts, which led to a much larger capital gains bill than I expected. What caught me off guard wasn’t that gains are taxable, but how hard it was to balance hitting a cash target while minimizing taxes.
This year the issue is a little different: with market uncertainty, I’m thinking about diversifying a concentrated stock position. I ended up building a spreadsheet to model lot-level taxes and compare sale strategies, mostly because I couldn’t find a simple way to do this across accounts.
Curious how others handle this — do you model after-tax proceeds before selling/diversifying, or mostly rely on broker tools, a CPA, or spreadsheets? Any tools or approaches you’ve found useful?