To better clarify, the stairs work exactly how I expected them to work. In fact, being able to jump off them is honestly quite nice as that wasn't the default back then. But the start isn't just small guys, there's also the bow ork on the bottom who'd get my ankles as I'm climbing and an ork throwing stones on the upper platform that would be ready to lob one straight at my head once I made it about halfway up the stairs. Those were really my gatekeepers when it came to getting to the shop. But, to be fair, I was also taking out the small guys at the start as they were pretty much free EXP and money, so that could have something to do with those orks always being ready to get me since I took a little too long each time I respawned. There was also the 3rd set of stairs which I couldn't get up as there was an ork right above it that just knocked me right back down for trying and they didn't wanna move at the time. I don't know if that was consistent as it was shortly after that where I started getting skill gapped on the first set of stairs, so I didn't get to go check. (Did some b-lining there to confirm and it doesn't seem to be consistent, but can happen if I take a little too long on the lower floor. Although, it also seemed like it had gotten stuck for me last time as I remember getting knocked down multiple times before they even considered moving, which didn't happen in my testing here. Got unlucky yesterday, it seems. It really was a horrible night for me to have a curse...)
I guess if the negative health is more a feature than a bug, then I'm more just not the biggest fan of the idea? Mainly because it can continue to rack up, like in my case of being bad at the game, to where it becomes a bit more of a money sink to restore your health to somewhere comfortable, which drains your resources in a way that adds a bit of insult to injury for me. It is fitting of the times, though, so it's like... hard to fully judge as it does kinda fit. I think restarting at low health (Maybe 5 to 10 could be a good number? Allows a hit or two before death, but still requires you to get potions) or having a limit on how low you can go in the negatives (Maybe about -10 to -15?) if you're wanting to keep that system in would be more how I'd approach it, though. At least, for a jam setting to account for skill differences.
At the end of the day though, most of this can be put into the category of... I was just bad at the game. My undoing could just be my greed, poor planning, and not wanting to restart if I didn't have to. I wanted to keep my gear without having to go back to zero as I was already restarting from the beginning anyways with negative health, which felt punishing enough without losing everything just to go get it all again because I had to restart. I still did very much enjoy my time regardless, so I hope that doesn't get lost in anything I've said here.