When we went up in size (the time before this) we didn't make a big enough jump because we wanted to stick to a budget, and we only held that boat 3 years then blew the budget on our current boat. I'm glad I did. Don't talk yourself into something if it doesn't meet your criteria.

However, considering your last line, do you really need the size boat you spec'd out? Only you and the Admiral can answer that.

Another consideration is your short season, and the fact that maintenance labor/expense increases exponentially as the size of the boat increases.

Yesterday we went for a daysail in 10-15 knot winds (true) and were reaching back and forth between Long Island and CT at a steady 8.5-9.5 knots (occasionally above 10k). It was great because I felt more and more relaxed, feeling like this is "the life" and all the Spring prep labor and expense is "worth it". When the stresses of daily life melt away, you can't put a price on it.

IMHO - Get what you want and don't settle for what's available locally unless it meets your needs. Go out of area if you need to, but if you blow your budget don't blow it to such an extent that it causes you to borrow or stress too much about the upkeep.