[loeg]

TLH is sort of a synthetic loss. You just sell and buy essentially equivalent funds to realize an unrealized but existing loss, lowering your cost basis. The amount of stock you own doesn't change at the TLH event. You get a (small) deduction against your taxable income at the cost of more capital gains in the (maybe distant, lower tax bracket) future.

[oplav]

If you participate in charitable donations and are able to itemize deductions, after a period of capital gains you can also donate the low basis shares and then rebuy the shares with cash immediately. This is effectively donating cash while stepping up the basis of the asset.

I’ve been doing this cycle for a bit now and while it doesn’t produce life changing savings, it does motivate me to donate more.

Donor advised funds make donating shares pretty easy to do.

[loeg]

Yes, that's true, and I do donate low basis shares. But it's a small portion of my overall portfolio. Big +1 to DAFs -- I use Vanguard Charitable.