When I was trying to scrounge up all the gold I could, I found that 1500 upkeep or so let me wear light mail with a good weapon. 2 Hours of playing might net you 5000 to 10000 gold if you get lucky with multipliers. 2000-2500 upkeep isn't bad. You might lose money if you have a night of constant x1, but overall you should at least break even. That's enough upkeep for some really nice gear.
As long as you aren't bankrupt, just wear what you like. The heaviest plate armor and horses are the ones that will drain your gold. If you can't stand your gold not slowly rising, try using a light set of equipment when you have x1, and break out the heavy set when you have x3 or more multiplier. Changing your gear makes the game more interesting too. Playing the same thing for hours can get tedious.