BUG: When the captured person wishes to repay you, selecting "Ask for material reward" and receiving an Item (not gold) the proceed through area progress bar resets if its at the last encounter before choosing a path to take
This has happened a lot to me although the chances should be sooo small. Needing a bandit and bystander encounter, then the bystander rewarding you, then an item reward, and finally all this on the last encounter for the area.
EDIT
BUG: When starting the game from Frostford then eventually getting to Winborn and purchasing the Teleport Gem, will result in -500G then removed from the shop (all normal) but when opening the Portals tab at the mansion, Winborn isn't there (I've also been to Gorn and bought that Teleport Gem as normal it does appear as an option to teleport to so it seems its just Frostford to Winborn)