The map making and map exporting might be worth it for me, I'll defo wishlist it! One of the things I am noticing is that a lot of the features you got overlap with the software I already use (FoundryVTT) and between already having DungeonDraft and Dungeon Alchemist. It's a hard space to break in to and I do honestly wish you the best.
The Workshop support is interesting, though I am guessing from your description that so far, it won't come even close to rival the module support that something like Foundry has.
You price point is very good though. Could be a solid entry point for a lot of GMs that want to get off Roll20. Oh yeah one thing that is not super clear from the Steam page as well is, does only the GM need to purchase the software or do players need their own copy too?
The Bard player still has to say the right things in the first place to make the check at all, there is not guarantee they will do that. But if they do... LET THEM this is literally their characters big thing! Why not let them do that specific thing? It feels backwards to me to have a "Well this fight has a conversation skill option but I am not going to let the character that has conversation skills participate".
IMO the rolls are not the interesting part of this, the party figuring out how they can get bad the guy to change their mind is.