William Weld seemed to have fun. He could take a joke and more than a few drinks, though looking back, he seems to have had more in common with Kerry than it appeared at the time. Weld seems to have been kind of a "half-breed," half-Brahmin, half-regular human being, who's gotten more Brahmin as he realized that he didn't have much of a political future. Buddy Cianci has the "common touch," and John Rowland looks pretty common, too, but that's not always a good thing.
Why have things changed? Maybe because money talks more in politics than it once did. You don't get points licking envelopes for the local party committee anymore. You have to appeal to the big contributors, who are a pretty homogeneous lot in their attitudes. You can't scare off the bankers and also have to look good on television.
Rhode Island may be a little more populist than Massachusetts or Vermont, but New England doesn't seem to do folksy any more. Maybe the whole country has changed as well. You don't find so many colorful characters in politics today. If any do rise, it's because the polished guys move up to Washington and turn over the reins to the local crew. Coolidge himself had been a lieutenant governor chosen to appeal to Western Massachusetts before he moved up to the governorship.
Kerry is the extreme case that illustrates the general rule: ordinary people don't get as far in politics as those with connections, money, and surface polish.