Your fixation on CRT before your virgin trip is not only normal, it is encouraged. It helps not only to inform you, but helps beuild excitement and anticipation!
Do NOT pay up front. That's one thing you got wrong.
Quantity vs. quality: Some guys feel that if you repeat with a given girl, you somehow lose power or control over the situation. My take is, if you find a good girl with whom you enjoy spending time, you can stick with her without ill effects. One possible, although not guaranteed benefit of repeating with the same provider is a discount on the price you pay, or more time, certain service (bareback BJ, anal) etc. It's definitely a case of YMMV. Also, the more time you spend with one girl, the more likely it is that you could become enfatuated with her. Bad idea.
Don't know about swimming or bicycling, sorry. Maybe local residents will comment.
Have a blast on your first trip to adult Disneyland!
Cheers,
Paul