Ok....first semi-serious answer ;)
H14T -- Never sailed one, but I think this boat would be a pretty
fair single handed cat. Light weight, easy to right, plentiful parts.
H16 -- Good boat, good for single or light weight duo. Plentiful
parts, advice and mods. Easy to right, lots of used boats
in good shape if your patient. If you go by boats built this
is probably the most popular multi ever made.
WARNING - Biased Opinion Ahead
P16 -- The best damn 16' fun beach cat ever designed. Deep
walled hulls for heavier single/duo crews. Dryer ride
for lighter crews. Can fly a hull in 12kts of breeze with
400lbs of crew wieght on the wires. Easier to learn on
and the fastest of the old school 16's. Larger tramp area,
can handle 6 adults for "fun" cruises. Rare boats to find
in any condition as most Prindle owners jealously guard and
care for thier "secret" weapon. Except for the mast extrusion
all parts are easily available, either used, or new from
Murrays.
I started on a H16, then went to a P16 when it was the only
boat I could find after a hurricane wrecked my H16. I never
looked back at Hobies again. Have owned and single handed
P16's, P18's and P19's. Told ya it was biased.
Nacra 4.7 to 5.8 -- Race boats. Fast and agile. I would not
however recommend these boats to a beginner. Parts everywhere.
Finding one of these in good condition is almost as hard
as getting a Prindle owner to part with his (or her) boat.
As always...your mileage may vary