Hard to say, but I think it boils down to conference.
The Holiday Bowl is usually Pac-10 vs. Big XII whereas the Gator Bowl is ACC vs. Big XII or Big East.
Generally I could see the Holiday Bowl having a better match up of better teams than the Gator Bowl. That's not always the case. Personally, I would like to see a game of Texas vs. Virginia Tech in the Gator Bowl, instead of a Texas vs. California...but that's just personal preference.
If you're trying to recruit West Coast kids...you better hope a Holiday Bowl victory.
If you're trying to recruit East Coast kids...you hope for a Gator Bowl invite and win.
As far as $ goes towards schools/conferences, I'm not sure. I would guess Holiday Bowl buts that's all it would be, a guess.