Although its supposed to be surfing season, this year's February was excellent in PR. We had good winds almost everyday.There were many 20+ knots days and some over 25.
The best Flat water spot in the island is Parguera - that's south west. You get to the launching spot in a boat. Launching spot is 2-3 feet deep water. Water is crystal clear, a huge area protected by reef and channels. Luijo from CaribbeanXtreme is the local kite instructor and guide. He has a huge boat and receives kiters from the states year round. His email is firstname.lastname@example.org
. He will take care of your accomodations, transportation, etc. He is also a Slingsht and Misfit rep.
In San Juan it's better for choppy waters and wave riding at that time of the year. The local instructors and pro's are Antoine and Phil at email@example.com
If you want to kite a day with big waves at Isabela (west), you can go with Luijo or the Carver brothers.
Night life in PR is always great and everything will be a lot cheaper than HI. Also, PR being part of the states, you won't need a busy, you'll use the same US currency and you get, along with the loca food restaurants, most US franchises and stores.
Hope this helps!