Thanks for the thoughts, esp. from another Gil in the world

They are all good ones. Yes, it seems like the big Q is why were the upgrades done, esp. the motor and tranny after 15 years. Electronics are usually minimums on charter boats, so those upgrades seem reasonable. The rig looks to have been updated recently. As to water entry, other areas do not show this... systems at same level as motor show age (pumps, water heater, etc.). But this is one to look into.
Of course we will have a thorough survey done, looking closely at structural components.
Why selling: Owners live in Carib and decided they do not use the boat enough to warrant the expense.
As for our cruising/living situation, sorry to not have provided this earlier. We will live aboard in St. Thomas (already live here in a house) on a mooring and cruise the Caribbean. No bluewater passages planned. Fuel =40 and water =200, so yes, fuel would be an issue outside of the Caribbean. Power will need to be upgraded to solar/wind (currently relies on high output alt) and a watermaker added. OW, systems are all set and many new.
We had looked at older more robust cruising boats (ex. Morgan 461), but the bank requires a newer popular boat such a Beneteau for resale reasons.
Thanks again and Happy Holidays!
Gil