I've set up a rail jam the past two years on my campus in PA and I can say first hand it takes a ton of time and patients. I'll throw it out there that it is very unlikely a resort would let you hold a rail jam on their property unless your being backed by company and a HUGE insurance policy(i think 1mil might of been the policy when i spoke with them).
I've planned some pretty large local shows and can say this is way harder but incredibly rewarding if you can pull it off. If you want shoot me a message if you have some more questions and i'll try give you a little insight.
Here's an edit from our comp last year
that was only our second year and it's growing fast!