Honestly IMO tax loss harvesting becomes very straightforward if you have a nice, simple portfolio of index funds. Your entire portfolio will be maybe 3-5 fund

Honestly IMO tax loss harvesting becomes very straightforward if you have a nice, simple portfolio of index funds. Your entire portfolio will be maybe 3-5 funds, so there really isn't much to keep track of. A few minutes reading the superficial loss rules for your jurisdiction should do it. (Generally, as long as you sell a fund at a loss and replace it with something similar, but tracking a different index, you're fine.)