I think as a story generator, it's fine. Life is random, but as a game, it felt like there was a little to much randomness I couldn't really make much decisions unless I got lucky and bought some items and spells.
On my first playthrough, I did not land a shop once which you can imagine how frustrating that'd be lol.
Don't get me wrong, I like rolling dice but I want to fail because it's my fault, if you know what I mean.
One suggestion that comes to mind is to maybe have persistent money/items between games and before the start of each game, buy your equipment then. For the maps, you could have tiles that are more likely to be something good, but also something bad, or neutral. That way, if you take more risk getting money or loot, you also have a chance to get more/better gear later on.
To be honest, I didn't really know how to work the encounter tracker, lol. Maybe some suggestions on how to use it?
The Heirlooms are a pretty good idea, I think. Not sure if there's a way to balance it with my other suggestions.
But I understand the point of this game, rules light, don't have to do much, just roll and watch things happen. So don't feel as if you must implement what I've said. :)