I believe you hinted at an interesting view on this topic in the original post: you had already owned your boat for several years and made up your mind about many things.
Sometimes I think it's a mistake for "new" sailors to spend much time online reading about "my new 44 footer" and "I'm so glad we're not smashed in the 28 footer any more." If you took this at face value, it would seem like no one would cruise anywhere on a smaller boat.
It's obvious that only a percentage of cruisers are going to stay with a smaller boat for all of their sailing lives, but that doesn't mean that starting with a smaller boat isn't a bad idea. The best way to find out is to have a cool Vega 27 for a couple of years, and find out.
We were perfectly happy chartering an Islander 28 with two kids aboard, and I think we could have cruised for a month in Puget Sound on her. We did similar trips on our C&C 27, and that affected the "size discussion" of our next boat purchase (a 34 foot) for our growing kids.
Anyway, I think too many of us "over research" boats and should simply buy small to begin (something we can easily afford) with the idea of letting go of it in a year or two if it's not a right fit. The idea of "getting the lifetime boat," especially at the start, is pretty misleading.
Sensible Cruising is a great book, even if it could use an update. (Disclaimer-- I have been pushing my brother to find an Albin Vega for his next boat.)