Those are some good points. Ok maybe not $$$, but if vb.com would go for it, free updates for maybe even just one additional year would be a cool way to say thanks. I mean heck, some of these HOTM's are the reason people even BUY vb in the first place.
A vb.org t-shirt would be nice too. I already think that you should sell vb.org shirts and hats. I'd buy one. (assuming it was a normal price lol)
Heh I'd buy a shirt. I like your idea about the extra year members area access. However the only problem I see is if someone wins HOTM every few months hense posibly adding up to 6 extra years or more of free upgrades for that person. There would need to be some type of may recieve the prize once every x whatever. However, they should still be able to win HOTM. If a hack that good makes it here they deserve recognition for their coding achievment.