My TV is a 2000 Land Cruiser, class 3 hitch and a electronic brake controller. I have a pair of airlift 1000 suspension bags in my rear coils too. The cruiser's stock suspension really sags with even a small cargo load of 500lbs.
I live in a really cool neighborhood, my neighbors that live on the bay know I am a mechanic and ask me all the time if I can run their water toys (boats and jet skis) for them so they don't sit forever. If I get the sail boat, my plan was to moor it in the bay and just use a dingy to go back and forth. One neighbor offered his dock but I didn't want to accept at the time.
Anyway, I will take the common themed advice here and rent a few times before I commit. I was planning on doing that anyway but I was put off by the first trailer. But winter is usually the best time of year to score a deal on a sail'er so if you don't hear back from me for a while, I probably went for the boat.
All and all you have been a really cool and inviting crowd, chances are I'll be back some day.
Thanks,
Dave