Hey there. I can spend in the neighborhood of 100k, including upgrades. Although I wouldn't want to go for more than 12-15 years old.
I really would not have any intention of selling it a few years later.
12ish years old, 100k, carribean, 35ish feet... sounds like a production boat to me.
I am not sure why you do not think a production boat (Catalina/Bene/Jeaunneau) would not be the ideal boat for this use?
The larger production boats are perfectly capable of offshore work. I've done it - many times and with kids. THey are not my first choice for crossing the Atlantic, but for your intersest should be perfect. We have a Catalina 400 and we have cruised on with kids. We are literally selling it all off to go out there F/T again for those very cruising grounds. I am even doing it with kids. THe C400 is out of your budget, but an older 38/380 may not be. I have owned one of those too. A C36 might do the trick. The C36 has some issues, but have also circumnavigated, so there are work arounds.
Just a thought.
If not, maybe an old Tayana 37? You can get some good feelers out in TOG (Tayana Owners Group). ALso outside of your year range.
ALbin Vega 27 to save a bunch of money but not real luxurious. Outside of your year range too.
THe Catalina 38 is actually the old Yankee 38 which is a SParkman Stephens design. Frank bought the mold from them and made some alterations to it, but I think basically the same boat. THink they quit production circa 1990 so this too is older than your preference.
I was going to say C&C but that also will be over your year range.
ANyone have other thoughts that can avoid production boats?