I have two stock accounts that I trade in, one is an IRA and the other is a regular account. I’m retired and I have a monthly transfer from my IRA to my regular account and keep the transfer amount such that I do not incur an income tax liability at the end of the year. This has been working well. However, I’m getting to the point in my IRA account, I may have to sell some stock to make the transfer. The good news is that with the zero trading fees these days, I could just repurchase the stock in my regular account.
However, and this is the crux of my question; some of the stocks I have in the IRA account are some of the old UWR and AP. I also have stocks in the IRA account that have been LI recommendations. So here’s the question, when I need to sell some of my stocks in my IRA to transfer to the regular stock account, do I sell more recent stocks from the more current LI recommendations and then repurchase them in the regular account, OR; do I sell the old stocks that I’m really upside down on IE: TUR, RIG, MBT, TEVA? If I sell the older ones, I know that is taking a loss, but would I be better off in the long run taking the proceeds and putting the funds to work in the LI recommendation or requrchase the old UWR and AP stocks?
Hope you understand this question.