if you run around in gear that's worth about 20k (it tells you on the equipment page of the website) you should make some pretty good money. You can't expect to make money if you're wearing "good" gear. That's just the way the game works. And if you want to find out why upkeep is in place, you need only read some of the posts in this thread to find out why.
Also on the equipment page tells you what your max upkeep is for a round (if every piece of equipment gets hit with upkeep). Besides weapons, your upkeep chance is 7% for every piece of equipment.
I can have low to medium armor (and a bec de corbin weapon) and still have these stats:
Armor:
30h 33b 38l
2/4Slots
16,990 goldCost
1,188 goldUpkeep (max)
Upkeep isn't a bad thing, and it's not as brutal as you're making it out to be.