...I'm still looking to purchase my first sailboat but when I started, I thought that a 28 would be fine. After experience on bigger boats, I thought a 30 would be the ideal boat. After more experience, I'm now set on a 32. If I wait any longer to buy a boat, I'll probably wind up on a 36 or even a 42 and will be living on it since I will lose the house in the divorce settlement.....
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.