Ratskinner
Adventurer
So the Discord theater of the mind based approach is the first thing I've hit on.
Can someone with experience review Fantasy Grounds and/or Roll 20 and talk about what it takes to make it work, and work better than just a chat room?
My group has just transitioned to Roll20. We use Discord for the voice chat, because Roll20 seems to really lag with that on. We use D&DBeyond for character gen, and a Chrome extension called Beyond 20 to link them to Roll20. Its a bit of a bear for the GM, if you don't want to spend a bunch of money. Luckily, one of our guys had a bunch of stuff on D&DBeyond already, so he could share it with us. Tonight was only our second session, and it went fairly well, once we got everybody on the same page.
Edit: the Fog of War/Dynamic Lighting is totally worth it. Players were griping a bit, but it was totally engrossing for the effect that it had on limiting their information.