I think upkeep is good in theory, but in it's current incarnation it's kind of broken.
To put things in perspective, my main has a dumptruck full of money. I could wear plate all day every day and it wouldn't mean a thing. I also have a higher than average multi from running with my clanmates. I have a feeling that there are a lot of people in the same position that I am.
However, upkeep is BRUTAL to new players. I made a new character recently and purposefully played him without my clanmates. The only time I was making any real money was when I was running entirely in peasant gear. I'm currently having him run around in 14k worth of gear and having a bitch of a time making any cash. If I have just one bad upkeep round, it took me anywhere from 3-6 maps to catch back up to where I was.
To me, it feels like you made more money as a new player before the upkeep system was ever rolled out. I don't want to go back to those days, however.
As it stands currently, I applaud the new players who actually stick it out. It must be frustrating as hell when you can't afford anything and pretty much everyone kills you.
It also seems kind of shitty that the only way a new player can get out of this money pit is by selling their 1st heirloom point. Imagine how disheartening it is to finally hit 31 and you have to sell your heirloom point just so you can use decent gear your next gen.
I don't really know for sure how to solve the problem, but I think that something needs to be done. One idea I have is a sliding scale of upkeep. For this, all upkeep costs would be lowered dramatically. However, the higher up in "tier" you go, the greater the chance of needing to pay upkeep on something. If we get the numbers right, higher tier equipment should cost about the same as it does now, but low and mid tier items would be much easier to sustain.
Thoughts? Ideas? Comments?