I owned a P-27 for 14 years, single-handing it for most of that time. It's an easy boat to single-hand, especially with an autopilot
. True, the winches
and mainsheet are forward, but that's when the autopilot
earns its keep. I could tack the boat by myself very easily by holding both sheets and then turning the wheel to the new tack. The boat balances well, and can definitely take more than you can. There are a couple of other current P-27 owners who hand out on this BB, but I'll send you a PM for how to sign up for an email list that has about 75 P-27 owners on it who will be glad to answer any questions you have.
As for what to look for in buying one, I honestly an not aware of any recurring problem areas with the boats. They are solid and well mannered underway.
My current boat is a P-33-2, so obviously I like Pearson's.