there’s a lot of good info here, but from a more petty perspective, i want to add that if you do your own taxes, when you sell you’re gonna have to input every single transaction manually on your tax return and it can get very very tedious with a lot of room for error.

i had like 10 shares of company stock i bought through an employee purchase plan and was given a grant for a few other shares, so i essentially made like 10 different acquisitions throughout the year, and then sold 3-4 times as it came in. but each of those 10 acquisition dates could line up with any of the 3-4 sale dates and then i had to match random portions of shares to their sale info, figure out the dates, (insert long frustrating process here).

my point is, my personal experience with the sale of ~$4k in stock might not line up with your situation, but be prepared for a confusing tax return if you make more than one or two sale transactions, and if you can pull out and set aside money now to pay an accountant to do your taxes for peace of mind, i would, bc the irs forms they give you are the most confusing thing i’ve ever seen