I don't see a problem with the upkeep, and I'm a str build. I consistently gain money with a x1 using straw hat, black lamellar vest, red wisby gauntlets, splinted greaves and a longsword. Since the patch I've only lost 6 body and leg armor, and I've made at least 85k since then, not including money lost from things I've bought. So as a recommendation, use slightly weaker armor at x1, and from x2 up use whatever you used before, and voila, insta-cash.