[willy]

The Jeep says it is rated for it, does it have a tow package, may already have a cooler on trans. How is the trailer and does it have brakes. Your trip is one I just took going even farther north, pretty flat terrain should be easy tow, keep speeds down, so what you get there an hour later. Check that trailer and if you don't know its been done get the bearings pulled, install new and grease. If it has brakes more the better. Tandem or single axle, either way got to have good rubber all around too, especially with single axle.
I wanted one of the other guys on this site to check that boat out, ideal set up for what he wanted to do, should serve you well, as far as price that depends on condition of hull, floors, stringers and especially the transom, along with engine. Conversation was had about how nice an sea drive is for converting to a bracket and outboard arrangement. Good luck to you, take your time and have a safe trip