It sounds like you're still entertaining the possibility of trailering...so, think of the boat models that would open to you if you could trailer a boat wider than 8.5', with the same size truck/trailer as needed for Cutwater, by the use of a simple permit available to boatowners who wish to trailer their boat?
Check your state DOT website for 'over dimensional permits'....there, will be found the topic 'permit for individual towing their own boat'.
You can tow up to 12' width without escourt....just corner flags and wide load banner.....permits are for one time transport, or an annual permit is available too.
Permit costs are minimal....in my state .one time permit good for 12 days is like $14....on the application they ask ' would you like an annual permit? ' Cost for annual is.....wait for it...$28 lol! And you can renew online..
If you cross a state line, then you will need the short-term permit for the window of time you expect to travel. An online permitting service makes this ez too
There is a requirement for liability insurance....states used to vary as to limit, but the standard has become $2m....you may well have that already...of not, the purchase of an umbrella policy in that amount will over ride all your policies, and is a good thing to have anyway....annual cost vary, but reasonable at $300 or so.
As to truck, a simple dually pickup...like a Ford F350 or 450 and a tri-axel trailer rated at 16,500# would handle a huge variety of boats. I would look for something 10-12 years old....no high end King Ranch or Lariat trim needed....just standard SE from any mfgr....perhaps you could look for someone retiring from RV 5th wheel traveling as this truck very popular....a crew cab is nice to have to carry extra junk too!