I'd say the system is a great counterpart to real life: as a peasant you make the most cash and can become filthy rich, as a high-horsed knight you go broke unless you become humble from time to time again...
I save up money during the first 20something levels, using good weapons but cheap armor (pilgrim, ragged, etc.), then can spend that money while I am on level 29/30 wearing my more expensive stuff whenever I feel like it. No problem once I understood how the system worked, and if I am losing money too fast, I go play a few rounds in my cheap stuff again.