monorailmedic

I'll add some additional information about keeping in touch while at sea, in case you find it relevant.
http://www.royalcaribbeanblog.com/2016/07/27/how-stay-touch-someone-your-royal-caribbean-cruise

You should be able to use your mobile phone on a terrestrial network once the ship is within 1-3 miles of a port.  Once in range, they shut off the ship's cellular network so that you stop connecting to it.  Keep in mind that while below deck coverage may be limited.  Also be sure your familiar with your carrier/plan's roaming policies and costs, as it can range from included, to ridiculously high metered rates.

I'll add some additional information about keeping in touch while at sea, in case you find it relevant.
http://www.royalcaribbeanblog.com/2016/07/27/how-stay-touch-someone-your-royal-caribbean-cruise

I can tell you what would happen if that was me 40,000 feet above the Atlantic..My wife would have told them to shove me out the door I have a cruise to go on!

No problem!
 
Finding a good TA is important.  You've gotta find someone you click with, that you feel is really working on your behalf.  I went through several before finding Brock w/ MEI.  

Yup.  When you check in it allows you to use your payment method for any individual or combination of persons in a given stateroom.  You can divide it up however you'd like.

My partner and I have always "checked in" using separate cards for payment.   You must do this when  the boarding at the pier.   At the end of your cruise, you will receive separate folios for your purchases which really makes it convenient and no hassles.  

Unless you're a light sleeper, I wouldn't sweat it too much.  Do I check what is above and below me (as well as next to me)?  Sure.  Do I worry about it if I'm not in an ideal spot?  Nope.  I can only recall one sailing where it was an issue for me, decades ago when we were directly below a dance floor.  Now, others may have had different luck, or may be lighter sleepers.
 
Another influence is where you'll be spending most of your time.  If you know that multiple times a day you're going to be in a certain loung, on a certain part of one of the pool decks, etc - then plan an easy path to get to that point.  Consider possible bottle-necks, like the elevators closest to the main dining rooms, etc.
 
All of this in mind, I really wouldn't obsess over it.

The Oasis class is impressive.  While I'm partial to more intimate ships, our Allure sailing with the RoyalCaribbeanBlog.com group cruise in Feb was an awesome experience.  While a big goal of my Caribbean cruise vacations is to relax, I'd make sure you try and cover as much of the ship as possible - there is just so much to offer.  One nice perk of this class: more deck space = no fight for deck chairs!
 
With regard to ports, I'm not sure your preferences, I'll share a few personal likes.  Labadee is a beach/beach activity day, and I'd take full advantage.  While the cabanas are expensive, I was sold on our last sailing - they're really nice to have.  If you happen to have a friend going on the same sailing you could split the cost, or just splurge - you're on vacation!  Next month we're looking forward to checking on some trails and areas part of the park previously present at Labadee - we didn't notice them until leaving but thought it would be something different.
 
In Cozumel we just like walking around.  It's an extremely safe and friendly city, and the best meals and deals can be had just a few blocks back from the main drag along the ocean.  
 
Falmouth has a secured port area with shops, but in my personal opinion, it's nothing special.  Outside of the port was some of the highest pressure selling we'd experienced in any country, and most don't like to venture out at all.  Since it's your first time, I'd be inclined to hit Dunns River Falls.  It's touristy, and common, but for good reason.  Be sure to book that through RCCL as any excurisons to the falls, Meagans Bay, etc are a bit of a bus ride, so the 'insurance' of the cruise line's excursion is probably worth it.
 
The rest of the time, like I said, enjoy the ship.  Check out this group of articles on the site all about the Oasis of The Seas!
http://www.royalcaribbeanblog.com/category/category/oasis-seas

Thought about it, but seems a pain.  I'd pay for the convinience of not doing that, but I reject the going rate of said convinience.  I'm hard to please.
 
I bother TMO pretty regularly (via customer service chat, phone, and twitter) about how great it would be if they'd follow suit and offer LTE in countries other than Mexico and Canada.  They have a highspeed package for international, but it's garbage.

To me, it seems Fi is that carrier - just doesn't work for the ammount of data I use.

I'm 100% with Matt on this one.  

There is a simple solution to the single supplement problem: take more cruises!
That's right.  Straight from RCCL's website:
Single supplement cruise fare reduced to 150% from 200% for members that have 340 or more cruise points

Welcome!
 
I've put some key points below, and at the end, a link to a great article on the blog that will provide some additional information.
Most people cruising out of Port of Miami prefer parking on site, though there are some off site options that are cheaper.  I haven't used them, so I can't speak to them.
RACE may assign you an arrival time, but know that you can show up around 0930-1030 and board pretty quickly (assuming they run into no issues with Customs, weather, etc).
As far as documentation, you'll need proof of citizenship in the form of passports, or birth certificates (passport recommended for a variety of reasons).  If anyone in your part has a name that is different on your passport compared to your reservation, you'll need name change documentation as well.  You should also bring your Set Sail Pass which you printed after checking in on the RCCL website.
When you arrive, you'll check at the curb any bags you don't wish to carry on yourself, you can use the printable luggage tags from the 'my cruises' area of the RCCL website, but the porters can help you if you are short tags.  It's customary to tip the porters here, just as at the airport.  You'll see your bag in the afternoon or evening in your stateroom, so be sure to carry on any medications, documents, or anything else you may need before the early evening.
Upon entering the building you'll show your Set Sail Pass and passport, go through security, then provide your documents to an RCCL rep who will provide you with your room key/boarding pass ("Sea Pass"), handle on-board billing, etc.
At that point, depending on if they're ready for passengers to board, you'll either board and enjoy the ship, or you'll wait for boarding to begin.  The Empress is a small ship, so generally the boarding process is very quick.
http://www.royalcaribbeanblog.com/2016/01/18/what-expect-embarkation-day-royal-caribbean-cruise

Premium will cover any alocoholic beverage (beer, wine, mixed drink, neat liquor, etc) up to $13, so yep.

That is all you need from the website (you can print out bag tagst here if you're checking any bags at the curb).
 
Make sure you have photo ID (DL is fine) and documentation of any name changes if reservation names don't match those on your birth certificates.  Also, confirm that your birth certs have raised seals.

That is all you need from the website (you can print out bag tagst here if you're checking any bags at the curb).
 
Make sure you have photo ID (DL is fine) and documentation of any name changes if reservation names don't match those on your birth certificates.  Also, confirm that your birth certs have raised seals.

Hei Ole, eg velkommen!
 
This site has lot of great information.  Be sure to check out the podcasts and Periscope broadcasts as well.
 
With regard to the rooms, I agree with bcarney, with two staterooms you'll have two restrooms.  Even with just two adults that can be a nice perk, but with a party of five it would seem the key to maintaining sanity.
 
You'll find staterooms on the Allure to be much larger than what you had on Monarch of the Seas, and there are far more options for stateroom type and location.  As you may have seen, the Allure offers staterooms that are part of the different 'neighborhoods' of the ship.  A Central Park Balcony stateroom, for example, is a stateroom with a balcony, but overlooks the Central Park are of the ship.  There are also Boardwalk Balcony staterooms, staterooms with an ocean view window, ocean view banconies, etc.  I personally like seeing the ocean as much as possible, and as such I'd recommend a Boardwalk room that is towards the aft of the vessel so you can see a glimpse of ocean by the Aqua Theatre, or, an ocean view balcony.  Of course, this is just my personal preference.
 
Take a look at the below link which explains the Oasis Class ships a bit, and let us know how we can help.
 
http://www.royalcaribbeanblog.com/2015/08/12/what-first-time-cruisers-need-know-about-oasis-and-allure-of-the-seas

Welcome!
 
I've put some key points below, and at the end, a link to a great article on the blog that will provide some additional information.
Most people cruising out of Port of Miami prefer parking on site, though there are some off site options that are cheaper.  I haven't used them, so I can't speak to them.
RACE may assign you an arrival time, but know that you can show up around 0930-1030 and board pretty quickly (assuming they run into no issues with Customs, weather, etc).
As far as documentation, you'll need proof of citizenship in the form of passports, or birth certificates (passport recommended for a variety of reasons).  If anyone in your part has a name that is different on your passport compared to your reservation, you'll need name change documentation as well.  You should also bring your Set Sail Pass which you printed after checking in on the RCCL website.
When you arrive, you'll check at the curb any bags you don't wish to carry on yourself, you can use the printable luggage tags from the 'my cruises' area of the RCCL website, but the porters can help you if you are short tags.  It's customary to tip the porters here, just as at the airport.  You'll see your bag in the afternoon or evening in your stateroom, so be sure to carry on any medications, documents, or anything else you may need before the early evening.
Upon entering the building you'll show your Set Sail Pass and passport, go through security, then provide your documents to an RCCL rep who will provide you with your room key/boarding pass ("Sea Pass"), handle on-board billing, etc.
At that point, depending on if they're ready for passengers to board, you'll either board and enjoy the ship, or you'll wait for boarding to begin.  The Empress is a small ship, so generally the boarding process is very quick.
http://www.royalcaribbeanblog.com/2016/01/18/what-expect-embarkation-day-royal-caribbean-cruise

There is a simple solution to the single supplement problem: take more cruises!
That's right.  Straight from RCCL's website:
Single supplement cruise fare reduced to 150% from 200% for members that have 340 or more cruise points

RoyalCaribbean pays agents a commission based on the price of the voyage itself.  To cruise lines (and other tour operators), travel agents are often a money saver, as they pass on much of the marketing leg work, customer service tasks (think reservations call centers, etc) to the travel agents.  They do train agents, provide marketing tools to them, speak with them, etc, but it's basically delegation.  Further, they know as a giant company, they have to maintain somewhat broad appeal, where agents can target more specific demographics, if they want.     Another way to picture this, is that when you work with your travel agent, asking questions about when formal nights might be, what the best ship is for your family's goals, etc - that is a conversation that Royal Caribbean would have to pay someone to have at one of their reservations centers, and frankly, those persons may not be as apt to answer, as they may not have sailed on the variety (if any) of cruises that the agent has.   For all these reasons and more, the pricing is the same.  In fact, there are many cases where booking through a travel agent can save you money.  Some of that is in simply helping guide you to make the best decisions for you, but there are groups that may offer lower prices through an agency (some that you may know you're part of, like RoyalCaribbeanBlog.com group cruises - others that are just agencies or travel groups committing to large blocks of staterooms), and an agent may help you get a lower price by repricing your sailing when new promotions come out, something cruise lines won't do themselves.   I certainly didn't cover all the details here, but I hope it helps clarify.  I'd add, finally, that to me, the service a good agent offers is enough that if I had to pay a small premium to use my agent, I probably would - but luckily none of us have to.  I book my trips via text message or short email, my agent has come to know my preferences, has all my info on hand, and is a great help overall, while offering me the same, or better pricing, than booking direct with a cruise line, hotel, car rental agency, etc.

I'm confident that all cruise lines value the safety of customers, or they have none.  It's simple business.
 
Keep in mind that while US travel advisories are good to be aware of, you'll note there are also travel advisories for Haiti, Jamaica, Mexico, Honduras, Colombia, and many other places that Americans (including US based cruise lines) frequently travel.  These advisories are there to ensure people know what's going on, provide for certain protocols for local embassies, and generally, provide the same advice that is prudent to follow anytime one travels anywhere.  They are also frequently specific to certain regions.  For example, the Turkey warning specifically advises American's to avoid travel to the SE of the country.  Kusadasi is on the central west coast, the better part of 1k miles from the SE side.  
 
It is not uncommon for other countries to issue travel advisories to the US.  Currently, Bahrain, The Bahamas, and the UAE have bulletins cautioning citizens who may be traveling to the US.  Again, these type of warnings are just to keep people aware of global circumstances, they are not indicitive  of imminent danger to the general public.
 
As you note, you have the choice to stay on board, and I think it's always important to watch our for your own safety.  I sincerely hope your sailing is enjoyable regardless of any global politics.

This is possible.  I'd love to know how the demographics look on Empress bookings vs Enchantment and Majesty.  It would seem possible that they're a bit older, as retired folks can go last minute more easily.  Just a theory though, no idea if that's the actual reason for the lack of night life.

This is possible.  I'd love to know how the demographics look on Empress bookings vs Enchantment and Majesty.  It would seem possible that they're a bit older, as retired folks can go last minute more easily.  Just a theory though, no idea if that's the actual reason for the lack of night life.

I guess another factor worth considering is how important is the Promenade as the central 'hub' of the ship?
 
I've heard great things about both classes of ships, but would your rather relax in the Centrum at the R Bar surrounded by glass? Or, would you rather stroll along the Promenade with its various shops and venues? 
 
It sounds like your decision is right on the line of small large ship (Adventure) vs. large small ship (Jewel)