I have a suggestion to help all players, old and new, of cRPG deal with upkeep in a fair manner. For lack of a better term, I'm calling this "finalizing" your character. The idea here is to allow players to wear heavier gear than they can normally sustain, something which is particularly hard on new players who don't have a million gold stockpiled or an infinite number of masterworks to sell to maintain their equipment. It also creates a more defined "end" for players who have a target build and set of gear for their character.
Finalizing your character would have the following penalties:
1. Finalizing is final. Permanent. The only way out is to kill the character.
***2. Finalizing resets your character to 10,000 gold. Your character keeps all of their equipment, including heirlooms.
3. Finalized characters cannot access the market.
4. Finalized characters do not earn experience.
5. Finalized characters cannot Respec, Skip the Fun, or Retire. (Skip the Fun characters cannot be finalized.)
Finalizing your character has the following advantage:
6. You earn more gold.
(7. You can finalize any number of characters.)
Allow me to explain #2: why should we reset the character to 10,000 gold? Old players have absurd amounts of money (Old Money!), which is what allows them to spend more of their time wearing heavy armor. If they are able to finalize and earn more gold, then they will simply be able to sustain even heavier armor for a very, very long time before running out. Some of these characters (okay, one that I know of) is actually fed gold by other players (one...). Resetting gold and restricting market access is designed to prevent abuse and even the playing field between old and new players.
Now for #6, which is self explanatory. How much more gold should a character earn? I cannot say for sure. It should be enough to carry notably "better" gear than normal, but still not enough to run around in the best gear all the time. I think a flat 50% increase would be sufficient and have a hunch that double would be too much. I highly recommend against making this based on character generation, because that once again shifts the mechanic dramatically in favor of old players. The gold increase may or may not be capped to a normal x5 multiplier as well, so you never earn more per tick at 5x than anyone else. Finalized characters should not earn more gold than other characters in Strategus.
For people tired of leveling up and just wishing they could wear sustain better gear, I think this is a fair solution to the upkeep "problem."