I'm very appreciative of those who share their advice and expertise here. I am now FIREd and moving from pretty much only buying investments to selling--either just for money to live on, or selling out of a brokerage account to continue to move money into my Roth. Here are the decisions I've made this week:
1. Decision: What to sell.
Early on I bought a variety of funds in my Vanguard account, before moving to a strategy of all total market fund. So my plan is to free up cash by selling off the other funds, choosing those with the highest expense ratio first.
2. Decision: When to sell.
I want to invest in my Roth for 2021 ASAP, and to do that I need to sell some Vang funds in my brokerage account and then buy in my Roth acct. I think I can do this as an "exchange" in Vanguard. I always try to invest my Roth money as early as possible in the year, and since the dividend reinvestment doesn't happen until March, selling this month should avoid the "accidental wash sale" issue I've read about. So the Roth money should at least be asap. After that, I need to come up with a better schedule than “when I feel I need money” : )
Decision: Choosing a cost-basis for sales.
I don't know if this is relevant since the market is at an all-time high, and with the smaller funds I'll probably be selling all my shares. But in principle, I understand going with the “Spec ID” option in choosing what to sell is optimal, so I'm going to go with that, and select the most expensive shares that are at least a year old. I think that will maximize possible tax-loss while not inadvertently making long-term gains into short-term gains.
Thanks to anyone who's read this far : ) Just writing it out helped me think it through, but if anyone has thoughts I'd love to hear them. Moving from buying to selling is a big step for me.