I had a 22 Seafarer and got the "two foot itis" disease.
Upgraded to a 265 Express then the disease hit me again.
Upgraded to a 330 Express and I (so far) seem cured (5 + years running).
As to cost of maintaining a larger boat - I don't see it any different from my 265 since both boats have twin engines and I do 95% of the work they need - myself. I don't do VST's and timing belts, otherwise, it's all fairly easy work. And cheap.
The ONE thing I will say is, the 22 footers are very portable on a trailer. The 30 plus footers are not. I'm talking trailering it hundreds of miles to go where the fish are. Of course some of you do this trailering with your Sailfish sized boats but that is a lot of beam and weight to be hauling down the freeway at 70 mph (just sayin). Special permits and big trucks are needed.
Also, if you're in between the 22 and 30+ footers, you are constantly challenged in the wet slip Vs. trailer argument.
I say, stay SMALL (22-25 feet) or go BIG (30-33 feet). If your situation allows for a wet slip, you will never look back. The beam of the 330 Express for example is 11'6" and waterline is about 30 feet. The comfort that these dimensions afford is considerably beyond anything that a 26-28 foot boat offers. And as to fuel economy - really not that much difference from a Sailfish. My 330 gets 1 nMPG on a day's fishing. I typically invite 3 of my pals along who help with the fuel cost and boat cleaning. As a result, for me personally, I have a 4 nMPG boat!
In summary, I have learned that "less is more" if you want to trailer your boat hundreds of miles repeatedly throughout the year. If your boating does not fit this user profile, go BIG and you will have no regrets...