I don't have much experience selling investments (we've been in the accumulation phase and don't really move stuff around much). I understand "cost basis" and how certain types of funds are characterized (contributions, earnings, conversions -- in the case of Roths). I'm an accountant so I've got a pretty good handle on the tax effects of different transactions. Most of our unqualified stuff is with Vanguard. Most of our retirement stuff is in 403bs, IRAs and Roth IRAs with TIAA (due to my husband's employment in higher ed.)
Because we will be mindful in our first years of ER of managing our income to qualify for ACA premium credits I want to be particular about the "character" of the funds with withdraw -- taking Roth contributions first and also minimizing gains on the unqualified stuff we cash out. I'm clueless about the mechanics, though, and how to instruct the investment companies that we want to sell specific shares.
Can someone please advise on selling strategies? Thanks.