It's not that bad. Use a gear loadout of around 25k "worth" of gold, Upkeep Max should be below 2K gold at the very maximum. You will slowly gain gold on average with 1X and will gain more rapidly if you get a multiplier. If you have REALLY expensive armor, only use it when you have a multiplier or excess gold.
For the most part you will probably want a more expensive weapon, and mid-tier gear such as mail. Try to cut back on things you do not use often, lugging around a bow and arrows is a bad idea, if your proficiency is low, and you already have an expensive weapon you use 90% of the time. This will help you focus your build, and be stronger in the areas you use most - and if you specialize in one type of weapon, your weapons break less often (based on your WPF skill)
You will have streaks of bad luck, it sounds like you had one for sure. Just keep at it, reduce the gear you're using - practice blocking so you don't feel you need to have the heavy armor - and you'll get the hang of it. Once you have a lump of money you can take care of those unlucky spells.
We used to have no upkeep for newer players. People abused it.
There still is no upkeep for newer players. You have to start paying upkeep in the mid-20's
or after you respec. Basically it doesn't do much.
Italicized the nerf that prevented the abuse.