Since there is still so much whine about upkeep, I'll just write how I can play with expensive gear and don't worry much about it. If you are a newbie who wonders why he lost the plate he just bought 3 rounds before, read it.
First, you simply have to accept that there is an upper limit of what you can use indefinitely. Yep. But that's good, since it prevents everyone filling all slots with the best gear, and then having elephant tramplers with tripple crossbows 24/7. It also makes the expensive gear more meaningful ... noone cares about your plate anyway when half the team has it. There would be only one other option to make such limits, that I can see, and that would be simply not allowing most players to get the best gear.
Now, I am able to maintain around 30-35k of equipment, and I am in the loosing team just as much. But that affords you some really decent stuff. For example transitional, fitting helmet and boots and a bec de corbin. Neither of these items is the most expensive, but it's all in the upper league and I don't feel particularily weak against the heavier options with it.
Leave away unnecesarry stuff. You want to be a melee fighter? Don't bring two crossbows to shoot people as they come close. Or make a versatile build with cheaper equipment. However, on the start of it try to take only gear that you think you'll need, and then try to use it in a good way (nope, running in plate after a peasant isn't, but it's your call really if you want to pay for that).
What you should do in any case, especially if you want to use very costly stuff regularily, is keep some cash in reserve, and some lighter gear (don't buy the most expensive items you can afford immediately, be patient!). Play in lighter equipment whenever you feel like it (and yes, you will have to take a backseat often, but that won't hurt you), your cash reserve will fill up, play in heavy equipment and it will drain, but as long as you keep the right balance you'll never have to go naked when you want to run around in plate.
And then consider to use the items tactically. Seriously if you get your plated horse injured in a siege you are a bloody fool. Consider the mid to higher tier items the upper limit, and the very best items the afterburner that give you the chance to really turn the tables when your team is overrun, but that can also drain you a lot.
