Holy hell, so no one has replied to this?
I do have a few comments:
- Belt has to be there. I would seriously make any and all attempts to make it out to New York if the belt were cool enough, especially if I can find some shithole hotel to hole up in, or coerce some unsuspecting dork into letting me crash. We're talking some serious cash even if I only scrub out at x-2 drop, but considering that I've actually done well at the past few events I've attended, I'm willing to risk that. In short, the Belt would be motivation enough for me to go, prizes to the entire Top8 just kinda sweetens it.
- $25 for a prize structure like that? You're a nice guy. Insane prize support in terms of Power cards aren't exactly necessary, but I'm not sure what cutting back on support would do. We Vintage players are kinda spoiled.
Say you're offering:
Ancestral
Walk
Ruby
Emerald
Drain
Drain
Drain
Drain
Why are you uncomfortable asking $30-35 for entry fee, and why are people today too afraid to pay that? I'm much more confident in my ability to Top8 in an event than I am of my ability to Top4, much less win out, and it is certainly worth me coughing up another ten bucks, especially considering that the best things in life are free: porn, pizza (for me - girl works at a pizza joint) and anything in a department store window at midnight.
Maybe things could be done like such:
Guaranteed Prizes:
1st: Ancestral Recall
2nd: Mox X
3rd: Drain
4th: Drain
...at maybe 40 people? Keeping in mind I have no clue as to the numbers and expenses on this thing, but 40 people at $30 bucks each should cover an Ancestral, a Pearl, and two Italian Drains, plus hopefully expenses (correct me if I'm wrong).
100+ people, use the prize support you mentioned, plus something incredibly special for the 9th through 16th slots - even if it's just a shirt saying "I top16-ed at TMD Championship and all I got was this lousy t-shirt", and then packs of 9th Edition to really rub it in

I'd have to say that a big part of it could be the experience and coolness factor of what they get. Custom playmats, shirts, etc.
I do have one suggestion for the TMD Champion's prize, but it would take some participation from this site and the forums - maybe a custom Avatar, Title next to their name, etc. Something personalized.
Should I forego scooping up that referree shirt that was on sale at Dick's and hang up my jock strap?
Huh?
- Pizza. NO wait, Ice Cream. Ummm... Pizza AND ice cream! Although they'd probably have to deal with the giant five gallon generic tubs of ice cream, because you can't skimp on pizza, man...
- 401K? Benefits? Dude, I don't even have dental.