Potential software nightmare, believe me, I know.
But, how about a different emphasis every time. One time could be about number of winners/consistency. Another about ROI/quality of winners. Another be a pick a longshot contest. Or how about one which is measured on best paying exacta or tri or super.
Maybe a maidens only contest or a turf only contest, or a rubber track only, or a bottom level claimer contest etc. Mix it up and have something for everyone at some point. The more formats, the more contests you can run.
Run a contest every week or every month. Hype them to the media. Use the contests as a draw to join HANA (restricted to members only) as well as a fundraiser for HANA.
How about team contests? Maybe East vs West? Or even Libs vs Cons
How about old folks against youngsters or men against women. Or old men against young women?
How about a freezeout with a set schedule of races that MUST be played. Miss and you are out. Last one standing wins
I suppose we would need a contest CZAR?