I will take you up on that offer.
That's a great story you have regarding your near run in with Cindy and Sheldon. Just shows how small the world really is.
I've been boating my whole life, as a child our family time was spent boating from Boston to the Cape and Islands almost every weekend.
My wife and I are on our 3rd boat, first was an 89 2155 Bayliner Cuddy, then an 02 Glastron Express Cruiser, and our current boat is an 06 Regal 3360; Fantastic boat but not the right one for long range cruising.
We used to trailer the Bayliner all over the place when the kids were young, but settle on Winnipesaukee 16-17 years ago.
Our current 3360 is to large to trailer with an 11.4 beam so we are lake locked, although we have talked about moving to the ocean, for a change. As you point out its a drag on the lake not being able to go for an "adventure". I've explored the entire lake many times, its time to find new territory.
We have considered and even looked at bare boat charters in the Ft. Myers area. Really not to expensive if you can get another couple to go in on it. We have family down there and visit every year but haven't pulled the trigger. I know that once we would love it.
I'm looking forward to your updates on your trip to bring you new Trolly home. Cheers!