Heh, Thats why I play Mongoose's Conan RPG (a variant d20 system). You start every adventure penniless and broke, and end every adventure rich. Then you go boozing and wake up broke again.
Essentially most weeks when you sit down at your table, you find out that your character spent all his money on booze, gambling and whores, leaving you with nothing but a loincloth and a dagger to your name (Dm's discrerssion).
Suffice to say in that system, feats and skills are everything. Equipemnt is a secondary thought. Its fun as hell.
Once you get above 6th level in DnD I never find myself worrying about money. There's always plenty to pay for dinner, rent a room and bribe a guardsman. At that point your never destitute.