I don't know Owlbear 1.0, but I've thoroughly enjoyed Foundry VTT. From what you describe, though, Foundry does not hit that same simplicity. I find it simple enough to use but it can also easily be extended with plugins to customize to your liking.
OSR/NSR Tabletop Roleplaying Games
Whither Reddit? In the meantime, here’s a place to chat up old school revival (OSR) and new school revolution (NSR) style TTRPGs.
My name is Todd aka Hexed Press and I am the current caretaker (have I always been the caretaker?). Here are some other places to find me, if you are so inclined:
Me personally, i like maptool. You can self host it and make a server for everyone to join.
Its not the prettiest or the absolute easiest to use when you first open it up, but you might give it a chance if you like open source projects and the privacy that comes with self hosting:
https://www.rptools.net/toolbox/maptool/
You can make maps, place tokens, write custom scripts for functions, and a whole lot of other cool stuff.
I really appreciate this, thanks!
What'd you end up picking? I was going to suggest just trying to get used to OBR 2. I agree it's not as wonderfully minimal as the original, but it's still not nearly as top heavy as Roll20, Foubdary and the rest, and the accounts, at least, are free. I've been running a megadungeon in it and the learning curve is pretty shallow compared to everything else.
I ended up goin with OBR2 but I'll be honest, I still miss the first edition.