I converted all my parent’s 8mm and all my home VHS to digital about 2 years ago.
I am very glad I did and recommend you do too.
Not because you’ll watch them often – I don’t because as you accurately point out they can be painful to watch – but because of the next generation.
We have grandkids now who are trying to figure our their place in the universe and family tree. They are just getting the concept that they will mature and that, at one point, their parents were little kids who lived with their parents. They’ll jump up on my lap while I’m at the computer and request that we watch old family movies. Watching old films and saying “there’s your dad when he was your age!” helps make it all click in their mind and certainly makes it more real than mere words.
If for no other reason than the above, I’d recommend you convert to digital before you start losing tapes to old age.