Our last shop was a tough one... we had just sold our 40 footer (owned jointly with partners) and were shopping for a boat 'just for us'.
We knew we wanted to downsize, otherwise we'd have likely bought out our partners. Initially we targeted 30 feet. I can tell you it's much easier to go from 25 to 30, or from 28 to 40 (as we had done) than to go back down.
We looked at a number of offerings locally and in WA state in the 30 foot range but everything looked impossibly small. In the end we settled on 35 feet. This was in 2004 before the crash hit the market and pickings were quite slim, esp locally where everything seem overpriced, trashed, or both.
We were not shy about 'no names', as we have never owned a Benehuntalina at any point in our sailing, this was to be our fifth boat. On our list of 'wants' was two good doubles (without converting a dinette), wheel steering, fractional rig, fin keel/spade, no 'projects', and our 'please' list included H&C pressure water and a fridge (which we had never really had)
In the end the boat we have satisfied most of those things, and has a pretty good 'row away factor' too. We found her in Poulsbo WA, had a tremendously positive experience with the seller, and now, 7 years later she's really coming together with canvas and upholstery updates, Max prop this spring, better sails, etc.
Our only beef/compromise that continues to niggle is that the cockpit is somewhat cramped and does not offer a really good upwind seated helm position.. but then again most of the time it's just two of us so.....
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)