You might want to ask your questions directly to the specific owners groups here on sailnet : Tayana, HC, Baba, Passport, Valiant, etc. Most of the owners groups have periodic rendezvous where many prosprective owners also are encouraged, etc. For example, there will be a Tayana rendezvous on the Chesapeake in early June. You might also want to actually join the individual owners associations (newsletters, shared info, etc.) until you firm up your preferences.
My T37 has the following warts: doesn''t sail at all under 8 kts; insensitive "barn door" rudder; teak maintenance; so-so metalurgy on original
rigging, etc.
Exterior Teak: not really a problem ... easily long term coated with the modern acrylic co-polymers. Teaky, Yes; Leaky ... not a bit.