SpeedNoodles

Unlikely. The area where Labadee is is nowhere near Port au Prince and is heavily guarded.

Veteran cruisers know to store their suitcases under the bed, thus eliminating space for stateroom attendant to hide. 

Thanks much

Unlikely. The area where Labadee is is nowhere near Port au Prince and is heavily guarded.

Unlikely. The area where Labadee is is nowhere near Port au Prince and is heavily guarded.

I'd start checking about 8-10 months before your sailing.  And once you purchase it, continue to check for price drops.

Unlikely. The area where Labadee is is nowhere near Port au Prince and is heavily guarded.

Unlikely. The area where Labadee is is nowhere near Port au Prince and is heavily guarded.

Unlikely. The area where Labadee is is nowhere near Port au Prince and is heavily guarded.

@AshleyDillo is correct. Just blow up picture with your finger. There are about 4 or 5 "huts" in photo along top deck. It's still very close to the pool. And you don't have to get up at dawn to find seats / steak your claim. But if not what you want or were expecting you can always still cancel.
Just a bit of advice. Do some research. Watch some YouTube tour videos of your ship. That will help you get a better visual. Then relax. My first cruise we didn't have message boards or YouTube tour videos. Well....we might have 2002? But it would have been news to me. Once you check out some videos, along with questions here. Relax. You will be much more prepared then most first time cruisers. First cruise is a learning experience and an adventure. Stay open to the excitement of the new. Enjoy.

I'd start checking about 8-10 months before your sailing.  And once you purchase it, continue to check for price drops.

I had the UDP on Icon. I get it on most Oasis-class ships.  We regretted getting it on Icon, though.   Not because the specialty restaurants weren't good, they were.  But there are SO many great complimentary or low-priced options that we were actually finding ourselves feeling obligated to eat at the specialty restaurants when we really wanted to eat at the AquaDome Marketplace or Basecamp.  If we hadn't done the UDP, the money we would have spent at Playmakers, Basecamp, and Izumi in the Park would have been far less than the UDP.  And there are no new specialty restaurants on Icon that weren't on our last cruise (Harmony), except for the Empire Supper Club (which was still an upcharge with the UDP.).
But, to answer your direct question, it was easy to get reservations at the times we wanted.  We just stopped at Giovanni's right away when we boarded the ship and made them all there.

My cabin was on Deck 8. I LOVED it.  So close to things that I needed!
Anyone with a beverage package will not get a receipt to sign.  If you want to tip extra, bring some cash.
You can take all cards with you to collect coffee for your group at Pearl Cafe.
You can get a ride share from Miami to Ft. Lauderdale.  It's a cluster and I had terrible cellular connection in the ride-share area, but others seemed to have no issues.  I'd personally wait to order the ride share, because I like to see what section I'll be waiting in (depending on how crowded each waiting section is).  Plus, you don't know if you'll be delayed getting off the ship or have any problems with Border Patrol.  But that's me.

Excellent.  Thank you for the reply and informative response!

My cabin was on Deck 8. I LOVED it.  So close to things that I needed!
Anyone with a beverage package will not get a receipt to sign.  If you want to tip extra, bring some cash.
You can take all cards with you to collect coffee for your group at Pearl Cafe.
You can get a ride share from Miami to Ft. Lauderdale.  It's a cluster and I had terrible cellular connection in the ride-share area, but others seemed to have no issues.  I'd personally wait to order the ride share, because I like to see what section I'll be waiting in (depending on how crowded each waiting section is).  Plus, you don't know if you'll be delayed getting off the ship or have any problems with Border Patrol.  But that's me.

The helipad is not open to the public on Oasis-class ships.

@SpeedNoodles thanks for all the great insight.  This has been exactly what I was looking for and couldn't find anywhere else. 

We did not book Hibachi at all, so I don't know if you can or not.
Our boarding time was 11:30, which was the earliest available that I'm aware of.  We had Express Boarding and got on board right away when they opened the ship up (it was the Inaugural sailing).  We got to Giovanni's around noon.  I honestly wouldn't worry about what's available in the cruise planner.  We also got the UDP at $243/pp (and still, we regretted it for this ship).

The way I'd play it is go up and see if there's anyone taking reservations at Izumi.  Maybe you can make them all there.  If not, Chops is right across from Izumi and you can do it there.

I had the UDP on Icon. I get it on most Oasis-class ships.  We regretted getting it on Icon, though.   Not because the specialty restaurants weren't good, they were.  But there are SO many great complimentary or low-priced options that we were actually finding ourselves feeling obligated to eat at the specialty restaurants when we really wanted to eat at the AquaDome Marketplace or Basecamp.  If we hadn't done the UDP, the money we would have spent at Playmakers, Basecamp, and Izumi in the Park would have been far less than the UDP.  And there are no new specialty restaurants on Icon that weren't on our last cruise (Harmony), except for the Empire Supper Club (which was still an upcharge with the UDP.).
But, to answer your direct question, it was easy to get reservations at the times we wanted.  We just stopped at Giovanni's right away when we boarded the ship and made them all there.

I bartend at my friend's higher-end brewery a couple times a month when he needs me (and when I'm not actually traveling for work, which is rare). The hourly pay I get with tips is just insane for the amount of work I do (and the amount of fun I have). 

I had the UDP on Icon. I get it on most Oasis-class ships.  We regretted getting it on Icon, though.   Not because the specialty restaurants weren't good, they were.  But there are SO many great complimentary or low-priced options that we were actually finding ourselves feeling obligated to eat at the specialty restaurants when we really wanted to eat at the AquaDome Marketplace or Basecamp.  If we hadn't done the UDP, the money we would have spent at Playmakers, Basecamp, and Izumi in the Park would have been far less than the UDP.  And there are no new specialty restaurants on Icon that weren't on our last cruise (Harmony), except for the Empire Supper Club (which was still an upcharge with the UDP.).
But, to answer your direct question, it was easy to get reservations at the times we wanted.  We just stopped at Giovanni's right away when we boarded the ship and made them all there.

Shorter cruises have their place but what I don't like is that many of the larger ships do them. 4 or 5 days on a Radiance class is fine but 4 days on an Oasis class and we barely have time to do all the things we enjoy.

If you want a better chance of warm weather at Coco Cay, then I'd pick April.  I've been to Coco Cay 5 times in Dec, Jan, and Feb, and never once has it been warm.  The last two times were only tolerable because the Coco Beach Club and the Hideaway Beach have heated pools.  The ocean was too cold for us to get into.