I don't understand your play postflop. You raised on the flop, although I think I would have made it a little more(not too much more, considering you aren't filled up!
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After that flop, I am getting my whole stack in against a maniac. You should have bet the turn more, probably pushed(which he would have called, no doubt.) Either that or put the rest in on the river after your weak turn bet. Like you said, this guy could have anything, which means he could easily have a hand you beat. And less likely he has a hand you lose to because there aren't alot of them.
Hand 2: I don't like your reraise preflop. Against this villian, you are never looking to bluff, and a raise on the turn with ace high is a bluff. He doesn't seem like a player who bets with absolutely nothing, which is the only thing you are beating right now on that board. Check/fold the turn. He wants to give you the money, don't be so impatient about getting it and get fancy and try and "outplay".
Never bluff this guy, ever.
Reload to $25. Never get so low...you want to make all the money you can off of idiots like this...and all the other ones.