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.