I recently discovered this thread (I've been busy and don't log on as often as I should) and I read all nine pages with great interest since I have always been interested in trailerable or transportable boats. Some people think that trailerable implies "legally" trailerable, i.e. less than or equal to: 8.5' beam, 13.5' height etc. To appease them I started calling boats that require an oversized load permit transportable. It is true that most boats could be transported, but some are much easier than others. Some boats have to have their flybridge or upper deck removed and may require one or tow pilot cars (which essentially doubles or triples the transport cost because you're paying for professional drivers by the hour). Therefore, I define economically transportable boats as boats that can be transported without costly modifications or pilot cars.
The main advantage of an economically transportable boat is you could make it large enough to be a comfortable live aboard (my wife doesn't consider any legally trailerable large enough to live aboard) and large enough to have some offshore capability.
My dream would be to get an economically transportable boat that my wife would be willing to live aboard. However, since economically transportable boats don't currently fit the reality of my budget, I purchased a Nimble Wanderer which is an affordable legally trailerable trawler like boat. Our experience with our Nimble Wanderer so far is that she is a hand full to trailer. At almost 10,000 lbs with a 3,150 lb trailer she needs a 3500 class pickup (I purchased a Sierra 3500 HD which does the job quite well). Also, the trailer/boat combination is ~37' long and 13' 6" high so you need to be careful where you stop for food and fuel.
As for those who are uncomfortable towing an oversized load, I'd say just hire professional boat movers to move it for you. Most people would only move their transportable boat twice a year, and the cost of transporting on land will be lower than in the water.
Regarding the Great Harbour TT35, I applaud their effort! They developed a more affordable boat with more accommodations than would fit in a legally trailerable boat. However, I don't agree with some of their design decisions. The biggest issue I have is with the choice of outboard motors. Outboards concentrate a lot of weight at the stern which requires a comparable mass near the bow. Since the moment of inertia is the summation of mass times distance to the center of gravity squared this contributes to a high pitch moment of inertia, which means it will be slow to respond to waves and more water comes over the bow. Also, I believe cruising boats need substantial electrical power, but outboard motors have very small alternators, which are only intended to recharge the start battery. The Suzuki DF60A has a 12 Volt 19 Amp alternator, which means the optional generator would be mandatory for me. Second, as a Mechanical Engineer, I think the air cooled generator is an intrinsically bad idea. Getting airflow to below deck engines is difficult on a boat and air has 100 time less heat transfer capacity than water. A water cooled generator would be a superior solution IMHO. I think the TT35 would be adequate for most sheltered water boating like the East Coast ICW, but I think the light displacement and shallow draft combined with a high pitch moment of inertia would restrict her to offshore use to fair weather. Finally, the "tailgate" swim platform looks like a good idea at first. However, using it in rough water is going to be very interesting. I'd prefer a fixed platform and a smaller transom gate with a raised threshold.
The SeaPiper 35 is interesting and could be transported with a little larger truck. However, I'm not a fan of the mid cockpit and going forward to use the head in foul weather could be an issue.
I would like to nominate Tad Roberts Enavigo 39
Enavigo 39 Classic Motor Yacht ~ Power Boat Designs by Tad Roberts or
Enavigo Power 39H - Enavigo.hr (although I like Tads exterior much better!) as a potential liveaboard transportable design. With a length overall of 39 feet and a beam of 10.9 feet it would be transportable with an oversized load permit and wouldn't require a pilot car on multi lane highways. The displacement of 18,300 lbs means it would require a capable truck (although my Sierra 3500 HD could tow it with a gooseneck trailer). The heavier displacement and 1 meter (3.28 feet) draft should make her much more capable offshore than the TT35 and slightly better than SeaPiper. I like the arrangements of Enavigo much better than the TT35 or the SeaPiper. Now, if I could just afford it!