I came across your post because I'm looking for a trailer for my 29.5. Did you just buy this boat last year? I saw the add for one with a Trailer in the mid west, but decided it was too far to go and purchased one on the Chesapeake.
At my club we ramp launch boats up to 31' on trailers. NOT EASY, but can be done. Here is what we do:
1) Our club owns a tow truck (1970's vintage). At high tide we use that to move the trailer to the ramp, block it and move the tow truck about 75 feet up the ramp.
2) We use huge straps (like the ones the boat lifts use) to reconnect the tow truck to the trailer
3) Then we unblock the trailer, let it go back till the boat can be floated onto the trailer
4) Pull the boats up the ramp.
5) Block, remove strap, hook tow truck to the trailer, and move to our lot for storage.
We do this with a handful of club members. It's a bit unnerving the first few you do, but we have done it for years without any serious issues or damage to a boat.
That said, I am in the market for a trailer, so if you are thinking you might be interested in selling yours, let's talk.
JR
SV Moxy
Bristol PA