Before I forget (as I won't be playing the game for awhile to let it develop further)
The biggest issue is the monotony. if you are truly using a tabletop mechanic you CANNOT under ANY circumstanes use the same two lines of text for encounters you will hit over and over and over again. I would suspect every box on that board will be hit several hundred if not several thousand times. Excluding the "round trip roundup and first introduction" its the same exact dialogue EVERY time. You can put a bandaid on this SOMEWHAT by randomizing maybe 5 to 10 different possible interactions (and I don't even know how that can be done with this type of game design) The best you could hope for is each of the job icons having different dialog at this point.
It feels like you are taking a game engine designed for a visual novel and stretching it for the gimmick of a board game. But since the game design is visual novel and not tabletop mechanic the randomization can only go so far. You are still beholden to recycling specific stills and specific dialogue boxes in a specific sequence. The only random thing is the spot you land on. The dialogue and the way it lvls is the same. It is way too generic. I don't really know what advice I give that you should take because some of it contradicts but unless you can seriously overhaul the tabletop aspect and put in A LOT more "text windows" give clear indicators of "progress to next lvl etc.....then I fear for this game.