As good as a Tayana 37 is, it is only considered good for the physically fit
and strong to single hand.

Most definitely disagree with that .... but for a reason that perhaps
you havent thought of: A TY37 has a relatively high CG thus a long
roll period. I personally now like a long roll period as I dont get so
beat up as when on a 'quick period' boat. I find I puke less when
slow rolling than snap rolling. ..... also much less tiring on long
distance travel.

I really dont understand the physically fit part as with good gear: BIG
winches, slick blocks and higher tech cordage its a breeze to handle,
comfy in a real blow, etc. Hell, with a boomed and vanged staysail,
she's a total self-tacker ---- dont even have to throw a sheet to
tack/gybe. If the genoa is on - just a single set of sheets to handle.
I race mine and find it almost boring in comparison to a fly-weight
'cork'. The only downside that I find to a TY37 is the huge sails
that when need to be removed/replaced ..... are too damn heavy (and
the ultralight super high tech fabric is 4 to 5 times as expensive).
..... lift 1000 sq. ft. set of 9oz. sails across a pitching deck
sometime and youll agree. Otherwise, IMHO - a TY 37 is an 'easy' boat
to sail (inertia/momentum)..

My wife has severe osteoporosis as a result of heavy chemotherapy, and
lots of 'missing' muscles .... with the proper gear she finds NO
problem singlehanding in most conditions - probably due to such a
stable platform. We used to campaign an ILYA scow .... she wont even
get on it anymore ... too physically demanding/tiring. SHE picked this
boat because of its seakindliness and easy handling (MY boat is still
the scow).

If I was in the market for a newer boat, Id definitely consider a
fractional rigged sloop - not as versatile as a cutter but easier to
power-up/power down.