In San Juan, I have never seen any hotel with a shuttle to or from the airports. I think there must be an agreement with the cab drivers not to have shuttles.
The San Juan hotel is nice. The street is much nicer than what the other reviewer is saying. We ate at numerous restaurants and find them to be pretty good. Like the Mexican one (left out of front door and across the street) as well as the Italian one next to it. Numerous outdoor cafes and lots of joggers.
The Ritz is a nice hotel, but the street around it sucks. There is no real place to eat outside of hotel area and the walk is dark & dumpy. I am not really sure how safe. Also, the Ritz is very expensive for food. Pasta is like $23 and steaks is $50+
By the way, the drinks at the San Juan is not as high as the above poster indicated. I seem to remember most were around the $6 to $7 range. Maybe it is the kind of wine that costs that much. If drinks too high, wait for Wednesday when drinks are free with the manager's reception.
I am platinum and have never gotten upgrades. I am on business so it is not that important. Not sure if I get upgrades if I ask.
As a note, the San Juan is very expensive in high season. Like $335/night in January + resort tax. In contrast, the Hilton down the road is at least $100 less.