Yeah, the first few pickups indeed make or break the run. There are some crazy powerful combinations and I kinda like it that way even though some of them outright break the game and trivialize the difficulty. But I don't like how it could introduce a "loot 1st chest & restart" tactic. Been thinking of a way to discourage that kinda like in Slay the Spire where you get a better start if you've reached the first boss on your last run. Slay the Spire is by the way the biggest source of inspiration on this game as it was the roguelite I was playing the most around the time I started the development on this. Never really played Dicey Dungeons (yet, on my todo list, love other Terry's games) but I can see the similarities.
The flame sword, crossbow and the hammer/apron are all very potent starting items with some powerful and well scaling interactions. I don't really hate that the different characters have kinda different difficulties but maybe the other two should be nudged closer to these power levels.
I admit I have restarted runs after getting the first chest, random encounter and shop. Being offered "Madness" and a small amount of gold in a chest, finding bread that removes 5HP and not being able to afford anything in the shop just isn't a great start.
Some encounters on the first floor (like someone demanding money) can influence whether anything worthwhile is available at the shop.....although beating someone that demands money is really low probability and I needed slime's help when I have pulled that off.
Setting up the available equipment pool on the first couple of floors to have something beneficial guaranteed might be one way to handle it. Each character definitely benefits from certain equipment more than others.
Powerful combinations are a bunch of fun. Shawl and Shaman Drum or Shawl, Chisel and Wisdom both lead to infinite HP.
It's a very satisfying game, all in all.
