I spend a pile of time on the water, and have owned a heap of different boats. Most of my sailing students come to the course ready to buy a boat. Usually their expectations are skewed because as first-time aspiring boat owners, they simply don't have an adequate grasp of how much money it costs to own, maintain and operate a boat. Moreover, most people don't get how quickly not only the costs, but the forces multiply as the size of the sailboat increases. At a reasonably young and fit 42 year-old whose spent his life in athletic condition, my 36' sailboat is at the absolute limit of what I can comfortably single-hand in rough weather. Anything bigger, and there's simply too much force involved.
Sailing on a friend's 44' C&C was delightful for all of the living space, but the owner, a former boat builder, lifelong sailor and cruising instructor for over 20 years, and 7x Vic-Maui veteran, admitted that his boat is absolutely beyond his and his wife's ability to sail without crew in moderate conditions. In my foul-weather gear, performing most of the heavy work during a 1 week cruise, there were jobs I did that should have taken 2-3 fit people, and I was frequently drenched in perspiration.
Most people who purchase a boat over 36 feet for their first vessel, wind up motoring, with the sail covers on, because they have simply purchased too much boat for their level of experience. The reality is that most people who cruise for more than a few days at a time, do so as couples. Most of the long-distance cruising couples I have met who own boats in the 30' range are glad they don't have more boat. If I didn't teach on my vessel, and just sailed with friends, I would cheerfully downsize to a 30' boat. All I really need to cruise on multi-week trips, is stand-up headroom. More boat length simply equals greater expense.
I know without a doubt that my fiancee and I would be just fine on multi-week cruises on a 30' boat, even with occasional guests along. Most of the people I've met who gave up on sailing after just a few years of boat ownership, started with much bigger boats than they might have. Had they started with something more manageable, they mights still be enjoying time on the water.
Just remember: buying a boat is like paying the cover charge for admission at a nightclub; now the expenses really begin - coatcheck, dinner, drinks, tips, taxi home. The price of admission is the cheap part.
Everyone is different, so no one piece of advice fits everyone. An awful lot depends on your personal commitments - do you have kids, what age, are you retired or work full time, and - most importantly - how often are you going to go out on the boat for 3-15 nights at a time? (Oops, I now see that your kids may be out of college, which could put you strongly in the cruisers category.)
A lot of people will tell you to go bigger because you'll end up doing that anyway. I went through the same process as you and placed unsuccessful offers on several 32 footers last year. Then it suddently dawned on me that our lifestyle would allow us to go away for a 1 week cruise once a year AT MOST. We were mainly going to be doing full-day sails, so the only real requirement was for an enclosed head. So I downsized my expectations to a pocket cruiser, and decided we'd charter any time we wanted to go for several nights at a time (which we still have not had time to do yet.)
What did I get for my smaller boat?
- A newer boat that was ready to sail at time of purchase, but still less money than any of the larger boats we were looking at
- A lot less maintenance and headaches (but still plenty of work)
- A boat that is easier to get in and out of the marina
- No regrets that we're not using the boat enough to justify the expense
- A boat that can be easily kept close to home instead of having to drive 1-2 hours for open waters
Everyone's different - but this is my thinking. At this point in my life, I'm glad I didn't get the 30-34 footer.