Lots of good comments here, BUT...

I'll return to shilling for Freedom by opining that absolute length
alone is not a decisive factor. For instance, under power in tight
quarters, I'd rather dock any 35 ft. fin keeler than a sub-30 ft. full
keeler.

Under sail, general handling while raising and lowering sails,
switching to engine, anchoring, mooring, etc. my experience has been
that a Freedom 36 (or 38) is infinitely easier to singlehand than any
"standard" Marconi-rig sub-30 footer. And yes that includes
singlehanding a tri-radial 'chute, which I wouldn't even try on most
keelboats.

And going to 40 ft., I'll remind y'all that Garry Hoyt singlehanded his
*engineless* prototype Freedom 40 all around the Caribbean, winning
races against full crews, and anchoring and docking in notoriously
crowded harbors.

And the Freedom 44 is essentially the same setup as the 40. So, AFAIC,
we're up to 44 feet and still comfortably singlehanding. With the right
boat.

Frank