Two points I can make:
1. Where you live in the Keys may make a difference. In Florida the maximum width for trailering cannot exceed 102" or 8.5 feet without a permit. The problem is that on public roads that do not have at least one through lane of 12 feet or more in each direction, vehicles exceeding 96 inches (just 8 feet) may be restricted by local officials (
http://law.onecle.com/florida/motor-vehicles/316.515.html). I recall a sign as you come onto Islamarado on the Overseas Highway (US 1) limiting vehicle width, although I can't remember exactly what it said. A cursory check of the internet did not help. The Keys are infamous for hassling trailer towers over width, tie down straps, etc. Just something you should check.
2. After years of mentally comparing express style boats (cruiser/fishing boat crossovers) and cruisers to the tug boat style, aside from their external looks I discovered there is another major discriminating difference. The interior of the tug boat emphasizes living conditions high up with large windows all around, while the typical cruiser has the living spaces down below–usually including the galley, head and dinette spaces. These interior spaces usually have small portholes (frequently non opening) at eye level or higher and a clear hatch or two to let in light, but you cannot sit and look out. The Cutwater manages to get more living space up high with great windows, but not as much as the tug boat which limits the down-and-dark space to the bedroom, where darkness makes sense. Even the head (except on the ≥29) is up above on the tugs with a giant window. Of course, a down side is limiting your vision aft on the starboard side with a head being high in the cabin.
You'll notice that on many ≤27' boats around you on moorings/anchor folks are sitting in the helm and co-pilot seats reading, resting, and hanging out as opposed to being down below in the living spaces, because they want the view and air.
Once you own and spend time in a tug (or Cutwater for the most part) you will appreciate sitting at the dinette, or working at the galley, or even sitting in the head with windows and light all around you, not to mention even above you. This was a major, unconscious, reason I moved from sailboats to trawler style vessels. Sitting "indoors" on a Ranger/Cutwater is a pleasure no matter what the weather; in a sailboat or cruiser with small port holes–not so much...