Liveaboard/cruiser for Puerto Rico

[Sentinel]

My wife just got news that she will be stationed in PR for the next 3 years, so we are going to jump in the deep end. We're looking for a monohull that will be well suited for liveaboard, and making random trips to neighboring islands a few days, maybe once a month. My question is that we are looking for a boat that will adapt well to these circumstances.
We prefer something with less maintenance (newer & less wood/teak)
Easy to sail (self tacking jib, bow thruster, etc)
Will do well with having a French bulldog on board (lower angles up and down companionway).
prefer prices no higher than 500k.

some thoughts so far are:
Jeanneau 440
Grand Soleil 46LC
Moody 45 DS
any other suggestions? I know these 3 are completely different vessels
I'm worried the 440 will be too light for these conditions?
lots of things running though my mind so I feel this is a good starting point

[sailorboy1]

All those will be fine

Don't over think it chasing the fansty of the “perfect” boat