I haven't been playing as much recently so not sure if it was a dagger or short sword but as far as weapons go, yeah, buying or stealing from the local shop is usually better even with the cheapest one as long as you get the right weapon.
I don't know how you can get rich as from my experience, you don't have much option of getting gold except finding some occasionally out in the wild but not much. I think as what the game is generally about, selling the player character is the only way of getting a stable income.
Haven't really encountered any one-shot battles yet or getting remotely close to starvation on my part. I'm either doing something right or wrong, lmao. Anyway, neat to have heard of your in game experiences.
Oh and as far as healing go, I think I just either go rest in the town or camp outside though I haven't noticed how much camping out would cost if any at all, I'll take note of that next time now that you mentioned starving.