While it's a subject that has been much debated previously methinks it's a topic that always attracts some interest.
I had a friend who cruised quite extensively in a 26'er and at the time he was positively obsessed with the idea that the perfect cruising boat was sub 30'. I crewed on that boat offshore for a short while and what became very apparent is that out at sea you really do need less than if you are e.g. marina hopping.
Nonethless I did find his boat and our PB which was 28' to be a bit tight on for space. I'd also note that my friend is now out there on a 60' ketch and the last I heard of him he was madly trying to find crew. I think he went from slightly less than sublime to the ridiculous. On the other LOA is not necessarily the best gauge of a boats size.
My point of reference is "can the two of us handle this" and in an emergency "can one of us do it" ? That of course ignores the financial situation and whether or not you can keep the systems going without too much outside assistance.
“Life is a trick, and you get one chance to learn it.”
― Terry Pratchett, Nation