Hi - I can't comment on the tax matters as I'm in Belgium...
As regards offloading the LEAPS, I've not done much of that either, and when I have I've mostly regretted selling as they went up and up and up afterwards. But my LEAPS are always bought in dips, or if not dips, then far enough in the past as to have DITM (except for the Jun 22 $3500's)
Now I've a bit more experience, my personal strategy is to either leave them to exercise (in 2022) or sell when the IV is very high/SP is at a local peak, in any case, don't sell them on a downward trend, as long as they're not aspiring too soon, hold them until a big SP upswing/IV increase.
But given that I'll need to pay taxes when I realise these LEAPS, I'm really tending towards exercising on expiry, unless something unforeseen happens where I need the money. Note that I cannot exercise these early, no possibility with my broker.
On the other hand, I fancy the stock will have split once or twice more before June 2022, so would be a substantial amount of money if I just leave them alone...