In late August, I put $20K into VTSAX. (It was sitting around because I was thinking I was going to replace our car. Ultimately decided against the car, and put it into VTSAX.)
Around the same time, I started an automatic investment of a small amount ($200) into my taxable investments every other week, also purchasing VTSAX.
I thought I would want to be prepared for a possible tax loss harvesting move with recent market activity, selling some of the $20K of VTSAX I bought in August, and buying VFIAX to stay in the market. Current losses on the $20K investment are just under $1,400. I have 5K of capital gains for 2018 that will be taxed at 0%, so I would need the losses to be over $5K before I even see a tax benefit. Losses over the $5K will net me 12% savings in taxes. Max reduction of ordinary income would be $3K per IRS rules, resulting in tax savings of $360.
I just switched my small automated investment to VFIAX in preparation, since wash sales rules are in effect for purchases 30 days before and after the sale that triggers the loss.
Anyone have any thoughts on my plan? $360 not worth the trouble? Losses of 8K unlikely? This is overthinking, just stay the course? Other feedback?