I always have to repair my stuff when I am like level 10 for example, is that normal or is it a bug? It gets sort of annoying...You don't pay upkeep until level 25 gen 1 [correct me about gen...]. If you above then you will pay here and there. The more WPF you have the chance your weapon will be broken is smaller. The longer your playing session is, your ratio earned gold/upkeep is more balanced. You can also untick checkbox "Automatically repair damaged items" but then your items will be broken and less useful.
1. You can make new character [called alt] which is also regular character. Just make new nickname when create new char [like in warband] and join any official server. Then you can develop it similar to main char.(click to show/hide)