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!