If stability is important to you then the Bombay should work well for you.
I get to the Caribbean every day
. I live on St Thomas and try to get out once a week for at least a few hours. I also race, but on a smaller and much lighter boat.
One other point I neglected to mention was that my boat has the deeper draft, 5' if I recall correctly. I am aware that there are many shallow draft Bombays around and I could not comment as to their sailing attributes or stability of the shoal draft version. What is the draft of the boat you are looking at?
My boat has also been repowered with a 2 cylinder Yanmar and from searching Yachtworld it appears many Bombay 31's had a single cylinder engine. I do not know how much horsepower difference there may be but into a stiff breeze and 5' waves I would appreciate a bit more grunt at times. The power plant may be something for you to consider also.