The word prompt for the 18th day of RPGaDay 2019 is PLENTY.
D&D, and most rpgs for that matter, work best when your players DON’T have plenty: limited coin, few magic items, scarce food or water…
Lack of plenty creates tension. It motivates the characters. It gives them are reason to be out there, endangering life and limb.
There’s your tricky situation. When your players have plenty, where is the motivation? A DM has to get creative. A DM has to threaten their bounty.
The DM giveth, and the DM taketh away.
That’s one of the things I always appreciated about Robert E. Howard’s Conan. For every victory and financial reward, there was always misfortune around the bend, usually in the form of a tavern wench absconding with his coin and turning him in to the local constabulary (after the Cimmerian had consumed too much wine, of course).
— Bob Freeman