I want this knowledgeable community to poke holes in my logic. I have stocks that have significant unrealized gains, and I have decent amount of cash. If I invest all the cash in VOO right now (close to ATH) and when market goes down, I sell VOO and buy VTI to maintain same exposure while harvesting tax losses against the significant realized gains *(yes, I will sell the stock with gains but won't have to pay any or as much tax)*. With this approach, I win if market goes up (VOO investment increases) and I win if market goes down (tax benefit).
Here's an example - let's say I invested $2k in individual stocks and have $10k unrealized gain in those individual stocks (i.e. total $12k). Additionally, I have $20k cash I invest in VOO and if this $20k becomes $15k, I sell $15k VOO to get $15k VTI and $5k in TLH. Now when I sell the individual stocks, I get $12k and need to pay tax on $5k ($10k realized gain - $5k TLH). As a result, I scan invest $12k cash in individual stocks. What am I missing?