[Imnimo]

This looks really cool, but I feel like there's just too many obstacles to using this with my group. Right now we use Roll20, which has a LOT of faults. Weird glitches happen basically every session. But it's free, and it works on everyone's computer, and those two benefits outweigh all its faults. To switch to TaleSpire, we'd have to make sure everyone is on a Windows PC (or know how to trick it into running on their non-Windows computer), we'd have to make sure everyone's hardware is capable enough, and we'd have to spend a collective $150 up front. And if anyone else wanted to jump in for a single session, they have to jump through those same hoops.

It feels like the sort of thing that will be great for groups dedicated enough to organize it, though.

[apocolyps6]

You should really take a look at FoundryVTT. Its a one-time purchase of $50 if you are willing to self-host it. I've been using it for the past year or so, and I've had almost no issues (none that reading the docs or asking my players to refresh the page didn't fix). The 3rd party support is great, some publishers (Fria Ligan at least but others too) sell modules for their rules systems on Foundry.

Here's a demo: https://demo.foundryvtt.com/join

https://foundryvtt.com/packages/modules