The situation at your co-op reminds me a bit of the one at our co-op in the sense that things are too vague. I'm a big proponent of contracts, of documentation, of clarity.

Our super currently runs to whatever supply place and gets whatever he needs or wants and we pay for it. It seems like a no-brainer to me not to allow that to happen. It all adds up and I know we're losing money that we shouldn't be losing--not because I think he's deliberately taking advantage of us but because it's simply too easy to spend money that isn't yours. I pushed to put an end to this and was told that his feelings would be hurt. But to me it just seems like good business sense to impose limits and protocols. The way it is now, it's like telling your office manager to order whatever supplies he or she wants, and not paying any attention to what is actually coming in the door and how much money is going out. On the one hand I completely understand the reluctance to alienate the super. But on the other hand: what universe is the super living in where no limits are ever imposed and there's no oversight?

Our super also has no formal job description. Does yours? Does anyone's? That's another thing I pushed for: clarity and boundaries would be as helpful for him as for us.

It seems to me that if your super had a formal job description, and more limits were imposed--not (and this is important) as a sort of punishment for him but so that everything is clear and above-board--you wouldn't be in such a difficult bind. What if you set about developing a formal job description with regular reviews and also formalized/put limits on his spending?