Bitcoin and Crypto Talk (Merged)(includes NFT)

I just got through what was a seven-year process of selling a company and each year had installments that were capital gains, generating significant tax (the company was long-held so the basis was zero). After the first year or two of trying to bank the proceeds and earn some interest until tax time, it was just too hard to avoid co-mingling the funds and then you get in the spot of having a big tax bill.

It's far easier to just send the money in at the time of the gain (you're supposed to anyway). Frequent trading doesn't quite lend itself to that (there's a bunch of events, not just one or a few) - but traders should definitely be sending quarterly tax payments to avoid this problem and be more disciplined about it.
Indeed. We had some self employed business people who were supposed to make quarterly tax payments and it wasn't uncommon that some would have to sell part of their portfolio to cover tax payments because they would either not pay on time or miss a couple of them during the year. Sometimes a client would also underestimate their tax liability at the end of a given year and the quarterly payments would not be enough to cover it. Definitely something to stay on top of.

Also, I don't know how the reporting is now, but in the past (i assume it's still the case), the IRS would assume all of the proceeds of the sale of a given investment was income and a tax filer would have to figure out and include the cost basis when filing their taxes.