I'm in a .net shop, and I've avoided most of the drama by sticking with .net 4.6/4.7 until now, and just ignoring anything to do with "core".
I'm sticking my toes in the water with the new .net 5 now, hope I've waited long enough.
that wasn't a good move since 3.0 it's really really stable, heck even 2.1 and 3.0 barley changed. 5.0 is basically just a package upgrade (well npgsql+efcore has had some trouble, but that took only a few days)
also if you did not use webforms it was basically also just a rename of using statements and impl classes between 4.7 and 2.x
If it's true that there's no real difference in libraries between 4.7 and 2.1, that makes me even more sure I made the right choice. I skipped a load of stress, and didn't even miss any important new knowledge.
There are a lot of changes. Don’t assume that poster is correct. A lot of the core HTTP stack has changed and a whole chunk of third party libraries are abandoned or rewritten entirely for .net core.
Anything async is likely to be a complete pain in the ass.