The upgrade is always a bit of work yeah. But that's pretty much the same with most commercial EDA as well...
For now, I keep 3 versions of KiCad (6, 7, 8 ) and when 9 is out, that'll switch to 7, 8, 9. That's to potentially avoid some new bugs on existing projects, but also just to be able to share projects, as many people tend to stick to older versions, especially in the professional world.