I've never had problems with the upkeep system until just recently, and that's because of arrows and the archery upkeep overnerf.
1h/shield during the new upkeep system was just fine: work low-mid level armor and I made money - slowly but surely over time. Every now and then I'd don heavy armor during x4s and x5s or use a mount, and that wasn't maintainable but that's how it goes.
Then I switched to archery... and am burning through cash wearing scraps for armor, a horn bow, a decent 1 hander, and bodkin arrows. It's really the arrows that seem to kill it, for no logical reason.
The biggest irony is that I can go horn bow 2x bodkins and a simple melee weapon and hemorrhage money, or I can go horn bow, 1x arrows, and wield a BEC or some other high end 2 hander, and I'll make money slowly. I mean, isn't that in part what this whole upkeep thing was about, to prevent stuff like that, or at least the ease of that?
TLDR: Revert arrow upkeep cost/break chance changes, they are prohibitive and silly.