Hi Jeff,As has been suggested, almost any decent monohull can be single-handed by some mix of a skilled skipper, in great physical condition, and with properly gear. But as a life long singlehander, the Pearson 39 would have to be one of the harder 39 footers to single-hand.
If you outlined the ideal design for an easily singlehander, it would almost be the antithesis of the Pearson 39. There are things that you can do to handle the boat motre easily in terms of figuring out your physical location on deck to be in during sail adjustment and course changes and how to time and sequence tasks.
I think that you have joined CHESSS and that should be a good source of information, and short handing resources.
Why do you feel the P39 is such a bad choice for single handling? Please be frank as I can use this information to perhaps make some additional changes to make it a better platform.
For a little past history on this particular P39, when her racing career was over in CT, she was professionally reconfigured with the aid of a naval architect to be sailed as a cutter, so she does not fly the huge sails the usual CCA-type boats do. In fact, her working headsail is only 95% and her main's foot has been shortened by about 1' to better balance with the smaller headsails. The staysail is also self-tending, so that is not a huge issue.
All of the lines have also bee lead aft to the cockpit and the traveler moved to the cabin top, so sail handling is fairly easily done. The decks are wide and uncluttered and the forepeak is open and flat. She is equipped with both a wind vane and autopilot, so she can be self-sailed for periods if I have to go forward for sail work.