Forgive me for being so dense, this is somewhat Greek to me.
It appears that I need to stay away from selling any VTSAX because of a contribution and/or dividend within the past 30 days in another account.
So now I'm leaning toward selling some VFIAX and exchanging it for more VTSAX. I still have contributions going to VTSAX, but buying more within 30 days isn't the issue, correct? It's once I sell something at a loss, I can't buy more of that same something in the time +/- 30 days (if I understand correctly).
So I've just changed automatic dividend and cap gains distributions to go to VTSAX from all other funds, so I shouldn't get a surprise dividend that falls under the wash-sale rule.
And now, the next bump is when I look under the gains for VFIAX, I have long term gains (positive, green) but short-term losses (red, negative). Do I only sell the short term ones? Once I get to this view and see gains/losses, it just doesn't seem as if my losses are that great compared to my gains over a long period of time. Am I missing something, or do you actually have to have lost real money in order to benefit from tax-loss harvesting?
Another option I have is to sell VGENX. There's a real loss there both short and long-term. What would be the best fund to exchange if I want to sell off VGENX? I've wanted to get rid of it anyway, but I feel like I'm so far in the hole with that one that I better just wait for prices to rebound, even if it takes 20 years. How bad would it be if I sold VGENX and exchanged for VTSAX?
Help! I'm hopelessly lost!