Upkeep works, just don't be stupid with your money. You use crossbow and bolts, expensive 1h and expensive shield, helmet, chest, gloves and boots, and on top of that A HORSE. Sure its all medium gear, but you're carrying a lot of different items and they add up.
This is what I did when I played cav.
x1 light armor on foot, 1h weapon, crappy shield
x2 medium armor on foot, 1h weapon, medium shield
x3 medium armor on horse, 1h weapon, medium shield
x4 heavy armor on armoured horse, 1h weapon, good shield
x5 heavy armor on armoured horse, 1h weapon, good shield, xbow or a lance
I ALWAYS made money if I upgraded my gear depending on multiplier.
And you're 4th gen, how are you a new player? By 4th gen you should have at least a few hundred thousand in the bank, unless you blew it all on looms, or was stupid and didn't manage your money right. If so, you deserve to be poor.