I had a trailer-sailer for a while. Unless you plan to stay out a couple days they are not really worth it. The set up time takes a couple hours once you've done it a few times and haven't damaged the rigging
up-stepping the mast
. Then you have to take it all back down again.
Never again would I have a sailer on a trailer unless I wanted to tow it to different far off places.
And if they are higher then a semi-truck (18 wheeler) you better know your height limit. I had to use an extended dolly to launch the thing at regular boat ramps. And I had short keels.