If you are interested in a Tornado I can try to put you in touch with a couple of people who had Tornado's for sale in your price range. Boats like this are not advertised anymore, these may be gone but there are others. One was a Reg White on a tilt trailer the other a Holt (Gougeon) wooden boat, I don't know about the trailer.
There are also Marstroms available, on tilt trailers they will run $11,000 to $15,000. This is probably outside your price range.
Most of these boats are in Texas. There are similar boats in the DC area. Get in touch with the active sailors ( the ones who interact with other sailors) they probably know of some.
If you want unique, the Holt may be a better boat. The wooden boats, as long as they have been stored properly and not abused, are more repairable than the older fiberglass boats. (Look at the pictures of how wooden boats are built, you could repeat any of those steps if required) The wooden boats take small dings a little better (more resistant to dints) and varnished boats look like fine furniture. Don't take the nonskid off the deck. A freshly varnished and waxed wet deck is slippery. You will look like a cat on ice until you fall off the boat
As far as trailers are concerned. You rig and launch a Tornado on it's beach wheels (there are a few exceptions). For trips over 150 miles, on a tilt trailer, it's much better to take the tramp off. So for regattas there is not a huge difference between tilt and non tilt trailers. For going to the beach, the tilt trailer wins hands down. In terms of rig time, it is comparable to the H20.
Tilt trailers need a 8-8.5 ft wheel width. They also need weight down low to stabilize them in crosswinds. A really good trailer will skitter sideways, instead of flipping in a cross wind. I have seen 4 types of tilt trailers:
1) Scary homebuilt trailers. (one day these are going to flip, drop the boat on you or explode when you try to tilt them)
2) Built from Class Association plans (OK depending state of repair and quality of craftsmanship)
3) Professional built (HEAVY mothers (1000-1500 lbs) can carry one boat tilted or 3 broken down, will survive higher cross winds and can be used as a light duty fork lift)
4) Exotic - Range from the better idea to the personal dream and from the awesome to the why?
(Note: if you replace the 1/4" valve with a 1" valve, the pressurized reservoir tilt systems can be used as a catapult. This is fun if you are throwing people into the water, not much fun if you are tilting your boat. The only excuse I have ever heard for this episode was "it seemed like a lot better idea before we sobered up" (names withheld due to threats of violence))
As far as sailing, the Tornado is a great boat. The classic rig is one of the few fast boats suitable for couples. The new rig needs 2 ~180 Lbm men working hard on the wire. These boats are awkward on land but make up for it on the water I have not found a nicer sailing or faster boat once you get to trap conditions. There are a lot of used sails available. It is possible to have a Tornado, with a spinnaker for distance sailing a new rig square top main for light wind days and a classic rig for high wind days. You can mix and match.
Tornado's are not surf boats. If you break a rudder, you will cry. They are expensive. This brings up another point. The cost of repairs is proportional to the original cost. These were expensive boats. There are a lot of used parts available but one day you will have to buy a new part that can cost twice what an old boat did. This why a lot of old Tornado are just left to die.
