So, i've played the game 4-5 hours recently. It is a micro lite solo rpg and with 14 pages of content, i'm okay with it not having a background hook but I can see how this would be useful vs when you start off in the mountain pass with no rationale for being there or having to come up with your own explanation. A simple table could have been incorporated
I do echo your sentiment a bit with the 2d6 bell curve of places largely being a burrow, meadow or deep forest. I did not play like this but I think your idea of rolling for locations would be quite good as it involves more location rolling and hopefully more variety and choice. So, when you are in a current location and roll a d4 = 4, when I played would just jot down 4 paths and choose a path, then roll for one location. However, having all four paths fleshed out with locations would allow the potential for other locations beyond the burrow, meadow and deep forest. I think if I was to play again, I would do this. When starting, I would probably include d4 paths going into the mountain pass and d4 coming out and could incorporate some background about why the PC is heading into the mountain pass (trade route, fleeing, appeasing the mountain spirt, negotiation with a village, peddling, musician, seeking help from next kingdom, etc).
I also agree that the 50/50 riddle encounter also seems a bit cruel but you do get to check off the place as visited. Maybe there could be a Points value which varies with location that you can try and solve.
My view, is that there should be more than 6 encounters and I think you could have incorporated encounters based on location or just more variety of encounters. Now, the Corny Gron Adventure Guide may expand on the ruleset and that is something I will look at shortly. You could also have different merchants who are harder to trade (use the Points system as well) with or could provide discounts (could it be the same merchant). I think selling could incorporate negotiation or a reduction in price if it has been used in an encounter.
I also think there are some polish to english translation issues and some of the rules could be more clear. I think having Hit Points (HP) and enemies with Points is confusing. Regarding your comment on combat, if you fail an attack, the enemy would roll their damage die and deal damage to you. So, with respect to "Failure means that the Enemy deals damage to you – subtract the points from your HP." Failure just means the enemy deals damage and they roll damage die against you and that is subtracted from your HP - which of course can be offset against the kaftan for 0 damage potentially. How its written isn't the best but I managed to make sense of that.