I’ve just about given up on going in June. Waiting to cancel that one.
Have another trip in Aug , which I’m still hopeful about but not optimistic. I would go in Aug if the planes are flying and enough things are open in Jpn.
This winter is very iffy with possibility of recurrent outbreaks. I may not book my Dec flights until literally couple weeks before.

For OP, the elderly parents factor is a huge one. If it were me, I’m not taking any chances.

Winter is a fantastic time to visit Tokyo as has been said by others.