Yes older items need more repairs.
Personally I find having items quite neat, they really need a lot of efforts to be repaired only when they are very powerful (read: prestigious and old), and I don't mind generally spending 50 gold on a new one. It's something nice to have after all, and +10% to some skill can be useful. I carried along a weapon +10% oratory wondering what the hell could be it good for and then the ambassador class came :p
