I believe most of the comments, observation and recommendations are right
on.

I had a good boat in my Cheoy Lee Clipper 33. Very easy to single hand even
though it wasn't well suited for a wind vane (ketch) I single handed it for
the 6 years I owned it for coastal sailing and in close quarters.

The only reason I built my Ingrid was because I had moved aboard and
realized that I couldn't spend the rest of my life living in such a small
compact accomodtions..

Now I have the room that I need but when I started building I was in my late
50s, now I'm in my mid 60s.. I have lost a lot of my strength from lighter
activities.. Winches compensate for lack of strength and I expect that I
will eventually regain my upper body strength..

However, in my observation, in the limited time I have been singlehanding my
Ingrid 38 cutter in and around the Pac.NW. The most difficult task for me is
dealing with the larger sail area (volume) and the weight of the sail
cloth.. Big difference between old limp rags on my Cheoy Lee and the
crisp(stiff) sail cloth of a 38 ft'er. Fortunately I have full batten main
with a Dutchman system (may change back to lazy jacks though). I expect the
head sails will be my biggest challenge when it comes time to change to a
different size in the roller furler (I don't consider it a reefing option in
the long haul). I ended up with 3 different head sail sizes. I expect I will
end up using the 110% most of the time..

Getting into too much detail here.

My point. I have two considerations. Liveaboard comfort since I want to make
my boat my permanent home and boat I can singlehand when a crew doesn't
materialize. Now the third consideration, is it too much boat as I get
older..

Will I end up sitting at the dock or in an anchorage because it is too much
work to get the boat ready for a weekend sail??

Must my thoughts, FWIW.

Steve
s/v Good Intentions