Pete,

I think the following would be good "appetizers" to see if you think (1) you or (2) your crew would be suited for the T-500.

Not necessarily in this order, but all right here in ole' FLA to reduce logistics costs:

Macho Man (day 2 optional) - Tampa -Always seemed to have a wide variety of conditions, from no wind to blast reaching. Also seemed to have a good pounding up the cost in chop. Day 2 isn't nearly as tough, but gives you a good idea of what kind of condition (fatigue, etc.) you'd face after a big day on the water.

Miami Key-Largo - Usually benign or pleasant weather conditions, but can be an off-water logistical nightmare. Good training for "Keys water" sailing (reefs/sandbars) and for getting your ground crew vetted.

Steeplechase- Key Largo- Probably best "T-500 Prep" race. Usually one or both of the days will be challenging weather conditions (wind over 15 kts. Upwind or blast reach in choppy water). Off-water logistics aren't too bad, since you can stay in same hotel the whole weekend

Keys 100 (former Hogsbreath) - Similar to Steeplechase, but logistics are more difficult

Hiram's Haul - Melbourne - Best "Taste of Distance" race. Short distance, logistics aren't too difficult. Protected water, which allows those in moderate shape to race in all but disastrous weather conditions.

RTI - Pensacola - Perhaps best "how long can I sit in this dang drysuit" test. Logistics are easy (one stop), but in all but the best years, you can expect to be on your boat more than 12 hours (in some cases closer to 24 hours).

Space Coast 45 - Melbourne - I think this is now held in protected water, which would make it a good race similar to Hiram's Haul Distance is slightly longer, too.

Everglades Challenge - west coast FL. Probably the most logistically equivalent to T-500. Never competed in it, but anecdotal evidence indicates the conditions may be slightly less ferocious than the T-500 on a bad week.

Any others I'm missing?