Puerto Rico safe spot
Most of the breaks can get serious at some point, the ones around San Juan can get crowded but there are usually lots of visiting surfers so localism isn't too much of a problem. A friendly spot is Aviones out near the airport, it gets smaller surf and can be a bit crappy but is friendly and is a beach break. Be very aware in PR. it has serious poverty and therefore some serious crime.
Heading out West of San Juan there are some very good spots, if the swell is not too high, Tres Palmas is an epic spot and along that part of the coast there is alot of fun to have on reef and beach breaks, be careful of the locals out in these areas.
If you survived the reefs of Maui you won't have a problem with PR but the rips can get serious especially around San Juan. The surf will be dropping off at this time of year and the mozzies will be increasing.