I'm going for a Kobold that employs riddles, puzzles and mind games within his dungeon. Eventually I hope to employ trap builders to fill the entire dungeon with all kind of death devices and puzzle rooms, he is either obsessed with knowledge or has an obsession for having power over others by knowing their dirty little secrets.
Tabletop Simulator is pretty good. I've never tried playing DnD on it but I have played other tabletop games with it and it really depends on how the program is set up. I would have to assume with DnD's popularity there are probably a lot of HQ games you can download.
20$ sounds steep for what is essentially a sandbox table top simulator, but with all the stuff the community is making, you'll get your money's worth if you play table top often. I'd watch some youtube videos of it if you're still unsure.
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