Place to live and school choice in San Juan/Guaynabo

I'd consider Perpetuo Socorro in Mira Mar for your daughter. It is in Spanish until 3rd grade, then English afterwards. I believe I spent about 8k on it per year. It has a good reputation that I believe is well-deserved.

We were considering that school also, but it seemed kind of far from the hospital (on Google maps).  Are there are decent places to live that would be convenient to that school and also not too far of a commute to the hospital?  We would like the commute to the school to be less than 15 minutes and to the hospital less than 30 minutes (less than 15 preferably).  Would living in Old San Juan be an option, or too far from the hospital?  Thanks!

Old San Juan sounds like it would be an option. It would be a 10 - 15 minute drive to Mira Mar in the morning and the school would be on the way to whichever hospital your wife will be working. I'm not sure which hospital you are referring to. Is it a hospital in Rio Pierdras, Auxilio Mutuo in Hato Rey, Ashford in Condado? If I knew the hospital's name, I could give better advice. Best wishes.

It's the University of Puerto Rico Hospital.  On Google, they also call it Industrial Hospital & University District Hospital (right off Highway 18 - near highway 17 & Hwy 1).

In that case, you have the advantage of having many options. Perpetuo is still an option if you live in OSJ, Mira Mar itself (where the school is located - Mira Mar is mostly made up of high-rise apartments - there are only a few houses for rent and they are big, expensive houses), Ocean Park to the east of Condado, or Isla Verde to the east of Ocean Park. You'll see on the map that Mira Mar is on the south side of the Laguna del Condado with Condado to the north and east. As an aside, people often don't realize that OSJ is actually on an islet and is connected to both Condado and Mira Mar by bridge.

The other good private schools are in Hato Rey (the middle and high school campus of Commonwealth-Parkville School), Guaynabo (the elementary school campus of Commonwealth-Parkville), and Condado (St. John's). You could live in OSJ and fight traffic directly south to your wife's work, dropping your child off at Perpetuo in Mira Mar, or if your child is of middle or high school age, dropping your child off at Commonwealth-Parkville in Hato Rey right behind the federal courthouse building. 

You could live in Condado and use either Perpetuo or St. John's, but Perpetuo is about the same quality as St. John's at half the price and the commute would be a little worse to the UPR hospital than from Mira Mar (but not that much worse).

You could live in Isla Verde. Isla Verde is made up mostly of high-rise apartments but there are a few houses for rent. You'd head west down route 26 to drop your child off at Perpetuo in Mira Mar or St. John's in Condado before heading south on routes 1, 22, and then 18 to the hospital. If you leave earlier than 7:30, traffic won't be too awful on the Isla Verde to Mira Mar portion of that commute but expect delays near the Tunel Minillas. That exit jams up badly everyday.

It would take you about 15 minutes from Isla Verde to Mira Mar. I used to do this with my oldest daughter, drop her off at Perpetuo in Mira Mar, then head a little farther NW into OSJ for work. Altogether it would take me about 30 minutes. But keep in mind that OSJ is right next to Mira Mar while you'll have to fight traffic south to get to the UPR hospital. Ignoring school, your wife could also commute from Isla Verde or somewhere else in Carolina to the hospital either via routes 26 and 22 and then 18, or via 26 to 17 to 18 (however, there's an expensive toll bridge on this route and 17 does jam up badly as well).

Cupeyville is a decent private school south of of the UPR hospital (in Cupey and cheaper than Perpetuo). You could live there, use Cupeyville, and the UPR hospital would be just north down route 18. Traffic would be jammed up on route 18 in the morning and afternoon but it's like that everywhere in San Juan for the most part. It is mostly unavoidable anyway and your wife's commute would be a simple one directions-wise - merely head directly north on route 18.

Ocean Park would be a good option. It is mostly made up of houses but has some apartments for rent as well, is to the west of Isla Verde, to the east of Condado, and on the coast. I have heard a lot of complaints from Ocean Park residents about rising crime and problems on their portion of the beach.

Some downsides to these neighborhoods:

I liked Isla Verde but it's not the most secure place late at night. It's not a war zone every night but I'd say Condado and OSJ are safer. Also, on the weekends, a lot of the kids from the local public housing project (located between Isla Verde and Ocean Park - reportedly the largest public housing project in the Caribbean) would invade the beach, smoke weed on the beach near the high-rises, play music with explicit lyrics at full volume all day with letting up, fight, and leave glass from broken beer bottles in the sand. Except for the actual fights, the cops were completely ineffective in dealing with the other antisocial behavior.

Condado can get very bad traffic jams. I've been stuck in a few that lasted for multiple hours without any real movement.

Mira Mar is a bit run down compared to its heyday and is not on the beach. It's okay.

Ocean Park is also a bit run down, relatively speaking. The roads are messed up for what you would expect in a tourist area and its not the safest place (not that any place is particularly safe in PR, tragically).   

Cupey is not the prettiest place and is inland without ocean views. It is also heavily congested and crime is a problem. Why live inland in baking hot metro San Juan when you could live on the beach (or a cool mountain air neighborhood)? Neither is it at a noticeably higher elevation, which would give you cooler breezes and maybe some nice views. You have to go farther south for that, which increases your commute considerably.

OSJ is great. Its architecture is hypnotically beautiful. But, it's crawling with seriously mentally ill / drug addicted bums who often defecate on your doorstep and eat out of the trash in front of your house. It also has frequent water shortages. If you live up the hill, your water pressure is bad and the water shortages are even more frequent. Also, parking is a nightmare. Definitely spend the money for a reserved spot in one of the parking garages (there are three but use one of the two near the entrance to the historic section, just before the federal building housing the post office HQ and the Bankruptcy Court (where I used to work).
 
Anyway, you have a lot to think about. Let us know how it goes. Good luck and Happy New Year's.

Nomad,

Just wanted to give you an update and thank you again for your insight.  We just returned from a week in P.R. and we signed a contract for a lease for a Condo in Guaynabo.  We also decided on the American Military Academy.  Thanks again!