You might just be on a rough streak. You shouldn't be draining the bank with that gear.
This. I use very similar gear (2027 gold , Military Cleaver, Heavy Round Shield, Red Tassel Spear, Guard Helmet, White tunic over mail, Mail gauntlets and Mail Chauses) and gain a lot of money.
Do you have wpf over 100 in at least one melee wpf (2h, pole or 1h)? If not, repair chances for weapons are slightly higher, and that could be the reason.
Another thing might be that you may not be getting some of the ticks. I have realised that sometimes if you have a menu open (esc, tab or C menus I believe) when the tick comes by you do not get it. Could this be the issue?