billdauterive

This is a great summary of tips.

The free picture (per person) is a very underrated perk.  I forgot about it my first couple of times but now it's a nice little souvenir to remember each cruise or port individually.  Now I have pictures taken at every opportunity and then just pick the best 1 or 2 to download free on the last night.

Yes, Explorer is the same as the rest of the fleet for craps.  $10 min, 1x odds.  $25+, 2x odds.  $50+ 3x/4x/5x odds.
I only play roulette a little but it's definitely a double zero (American) wheel.

I'm Prime with 13k+.  I was on pace for Signature earlier this casino year, but I'm fairly certain they changed the formula for points on craps.  The last 2 cruises I've been on I only earned about half as many points as I would have in the past.  I even verified they had my avg bet and time at table correct so a formula change is the only thing I can come up with.

Ask and ye shall (probably) receive

3x disowned isn't that much worse from 1x disowned.
Go big or go home.  

We actually booked one of the “complimentary for one person” offers recently.  It was the oddest thing…so long as we stuck with the interior offer, it included both of us.  When I tried to upgrade to a higher category, suddenly they wanted to charge for person #2.  So for the first time ever, we have an interior booked !  Yikes !  I plan on hitting the RU HARD when it comes around.  It’s only a 4 night on Indy, so I guess I would survive if I don’t get any upgrade….but I won’t be happy !

Pretty similar to me.  Those comp plus buy 1 are beyond worthless.  You can usually get the 2 full price fare through your agent for cheaper than the 1 comp + casino rate.

Congratulations!
A few tips:
Make sure you specify whether you are using your diamond drinks or not when you order.  Waiters will often apply them automatically if you don't specify and you may waste one on a low cost drink.
The coffee machine in the Crown Lounge is an underrated perk.  They also have a nice hor dourves set up at happy hour and a waiter to get drinks.
The concierge located in the Crown lounge can do a lot of things you used to have to go to guest relations for.
The free photo (each) is another nice perk.
 

I’m currently on Vision, I’m very impressed that the casino has so many new machines (unlike Anthem). 
anyhow, as I was playing my machine a “pop up” occurred on the account/points section of the machine stating someone’s first name and last initial and their winnings. I’ve never seen this before. Also popping up on the screen was an announcement for a “special slot tournament for St. Patrick’s day -see host for details”. I think this casino can program the messages for machines!
I mentioned to the casino host about the name/dollars win and she was mystified. She also said it sounds like it violates privacy.  She asked if I saw this again to take a picture and show it to her.  When I saw her later and showed the pic she said the slot manager was aware. 
not for nothing, my table mate at dinner has a very unusual first name, her name popped up as a $10,000 winner.  This is information I wouldn’t know unless she chose to share it with me.  I wonder how long this “information sharing” will last. My first name and last name  initial popped up as a $556 winner. (Smallest win popup) Unfortunately it was not me!  Now what if my husband or friend was playing in the casino and thought it was me and I deny it?! Will they think I’m lying?  What if it’s a non trusting spouse? Can you imagine the fights?!
side note-Allen B is winning lots of money.  Should I wait around a dark corner?

I was on this exact same cruise as @Matt and agree with most everything he says.  I know he doesn't specifically call out Sydney, but it's a good indication of what to expect from a fall New England cruise.  Let's just say I enjoyed it so much, I booked it again this year (minus the Bar Harbor stop of course 😞 )
https://www.royalcaribbeanblog.com/2023/10/30/first-new-england-cruise-what-surprised-me

The area around the port is really walk-able and very little vehicle traffic so I wouldn't be too hung up on making exact plans but be open to calling an audible as far as eating establishments go.  All the little house museums near the port are interesting and don't take up much time but give a good insight into the history of the area.  There are several pubs that are nice and one we went to had a fiddle player playing traditional Scottish music which was really cool.  There's also a nice little cidery close by.
Basically I was very surprised at how much I liked this port.  It's a great one to not really have a set plan but just kind of wander around until you find something that seems interesting to do/see/eat.  We were supposed to do a tour of Fort Louisborg, but it was cancelled last minute, hence our need to just wander around that day.  In fact, besides Bar Harbor, I think this was my favorite port stop.

Keep us up to date how this goes.  I'm curious about it too, especially since you're going to try and apply it to a cruise that will almost definitely be on a blackout date since it's over Christmas.

Keep us up to date how this goes.  I'm curious about it too, especially since you're going to try and apply it to a cruise that will almost definitely be on a blackout date since it's over Christmas.

Excited to share with you all the CREW NEIGHBORHOOD onboard the Icon Of The Seas!
 
This is an exclusive first look into our home away from home, whilst we work onboard the ship!
 
 

This has been and will be true for eternity...

Good point.  No need to worry too much about the private destinations, they won't leave without you there (but not for a reason you're going to like...)

Maybe time to bring our own hidden cameras so we can spy on the cabin attendants when we are out of our cabins.

And ALWAYS double check what the ship time is before getting off the ship.  I always check the time in the app as well to make sure they sync.  I've heard too many stories of people almost or actually missing the boat because they were on local time and not ship time.

I don't think that matters.  The casino only has a certain amount of cabin inventory available to them.  So the ship can be almost empty but if the casino inventory has already been taken then you won't be able to book it on a casino comp. 
i.e. booking a room on an non-comp fare in hopes to "save" a cabin for yourself to book a casino comp later won't work, it's 2 different buckets of inventory.

Great observation.  I completely forgot about the California requirement for shore side power.

There's also a self guided audio tour for free from the National Parks Service app.
https://www.nps.gov/thingstodo/walk-the-freedom-trail.htm

I'd recommend just taking an Uber to the start/end of the Freedom Trail and just walking it if you're physically able to.  There's so many sites to see along it that it can easily take up a full day and yet each stop can be just a quick picture or hours on end if you want.  Most stops are free (or at least freeish) except a few that have a nominal entrance fee.  The North End by Paul Reveres house also has a lot of restaurants for lunch/dinner. Cheers isn't far from the start in Boston Common so you could start there.  It's really close to the port so the Uber shouldn't take more than 10-15 mins (depending on traffic of course).  We enjoyed it so much last year we will probably do it again this year and just spend more time at sites we enjoyed and try different restaurants.
https://www.thefreedomtrail.org/sites/default/files/content/page/hero-image/ft-map.pdf

I don't think they will do very much to Quantum guest areas. 
The dry dock is being performed due to required maritime maintenance every 5 years until a ship is 20 years old then every 2.5 years.  That is the primary reason for the dry dock.  The required maintenance is the basis to maintain the certificate to sail.  Without the prescribed scheduled maintenance the certificate to carry passengers would be revoked.  
It's not unusual for some additional work to be performed to guests areas during a dry dock because the ship is empty of guests.  When Anthem was scheduled to go into dry dock in 2020 before the pandemic happened Royal flat out stated there would be no meaningful updates to guests areas.  They might replace things like broken floor tiles but there would be no new venues.  During my January 2020 cruise on Anthem they replaced all the carpet in the Windjammer doing sections every night while the WJ was closed.  This was months before her scheduled dry dock in May of 2020.  The point being that replacing carpet doesn't require a dry dock.  Carpet is routinely replaced all the time as required over the lifecycle of the ship.  
Quantum, Anthem and Ovation are one year in age apart.  Once onboard they are nearly identical to each other. In many places if you were magically teleported between ships you would not be able to tell which ship you were on since they are nearly identical to each other.  There are minor differences such as the name of the pool side restaurant.  Ovation had this restaurant changed to a Fish & Ships venue during her first Alaskan cruise in 2019.  I was onboard and watched them work on it during the cruise.  It didn't take a dry dock to get this venue changed, it was done during a regular cruise with guests.  On Quantum specifically they may choose to modify this venue in a dry dock, or not.  Bilingual signage might be replaced, or not.
The SeaPlex pods that hang off the ship where Playmakers is located on Odyssey is wildly different between the original Quantum class and the Quantum Ultra class Odyssey. They would need to do a lot of work making significant structural modifications that would alter the weight and balance of the ship requiring her to be reengineered and recertified.  It's possible but it would be costly.  Would a PM generate enough new revenue to justify the multi-million dollar modification?  Without a PM guests find somewhere else to drink and eat so the investment would need to show that retrofitting a PM would generate new additional revenue that would not otherwise be spent.  
I doubt they would make this sort of investment on the original Q class ships but who knows?
They could maybe find a way install a Teppanyaki venue by displacing the teen/kids club area.  That would require some infrastructure such as plumbing and electrical to support a food venue in a place that doesn't have that infrastructure currently.  Would such an investment generate new additional revenue or would it simply drain revenue away from the existing specialty dining venues?  Royal has data to review from Odyssey to see if Teppanyaki has created new revenue or reduced the revenue from the other venues.  If the amount of new revenue is minor it's difficult to justify adding a Teppanyaki to the original Q class (non-Ultra).  
My gut is telling me that the original Q class ships won't receive meaningful updates to guest areas.  If a ship does not yet have shore power capability that will likely be added during a dry dock.  This type of modification may be best done with the ship completely dark, no power.  A dry dock while doing other required scheduled maritime maintenance is an ideal time to slip in a few days to add shore power capability.  Quantum needs shore power capability to operate from California so if she hasn't already had this added, it will be added during this dry dock.   
I think they will find a way to refresh Allure and Explorer.  Adventure is mostly "amplified" already, they just need to some minor stuff to call it a full amp.   PM on Voyager class is not required to declare them amplified so I'm not sure Adventure will get a PM.  Royal has to be careful as they have told investors they are focused on reducing debt, not so much on amplifications.  Yet we all know ships like Allure and Explorer need an update.  Liberty and Adventure to a lesser degree but both could use a minor touch up.  That's four ships that clearly have a need despite Royal telling investors amplifications have been indefinitely postponed.   I suspect they will find a way to quietly update these four ships without the fanfare and telling the worlds about it like the "amplification" program did.  Beyond these four ships I don't see newer ships such as Q class getting meaningful changes such as new venues at this time.  

It gets complicated quick.  
A few senators have tried to introduce bills but they never go anywhere because it's not as simple as just allowing select ships i.e. cruise ships to do something as the act addresses all or nearly all commercial vessels that carry passengers.  On the surface it seems simple but it quickly becomes a pandora's box involving international law and maritime treaties. 
While the US can enact legislation that applies to US flagged ships, creating law that applies to foreign flagged ships isn't as straightforward.  In some cases within international law or maritime treaties there is only a concept of a vessel without distinguishing a modern cruise ship (which didn't exist in 1886) and a small boat that carries 10 people.  The US by itself can't rewrite international law or maritime treaties.    If the US was to chose to allow a foreign flagged cruise ship to carry passengers between two US ports (coastwise trade) then a foreign government could interpret that as being any vessel of any size can carry passengers between US ports because from an international legal perspective there is only the concept of a vessel.  That's overly simplifying it, but it's just one aspect of one complication.  Allow a cruise ship and you allow foreign ferries, water taxis, duck boats, etc. by the same modification.
Technically the aspect that impacts cruise passengers the most is a matter of cabotage and that is also evident with the airlines.  An Air Canada plane can fly from a city in Canada and land in a US city to drop off passengers or pick up passengers to fly back to Canada.   What Air Canada can't do is land in one US city and sell seats to reach another US city.  That is protected so that US domestic airlines compete on those routes.  That is an example of a cabotage regulation.   Just as Delta can't fly to Montreal and sell seats to carry passengers to Toronto.   There are international agreements involved.  Similar cabotage regulations are baked into the PVSA for passenger vessels but cabotage is just one small component of the PVSA.  
Once you decide to revamp such an old set of laws its difficult to just focus on only aspect of the law, i.e. cabotage.  If you are going to modernize law you need to look at the whole thing.  Cruise ship passengers probably don't care about the act and everything involved, they just focus on the cruise they want to take.  So in their minds it's just as simple as saying cruise ships should be allowed to do the cruise I want to take.  It's not that simple.
Keep in mind we are talking about a cruise industry that is comprised of foreign corporations operating foreign flagged ship.  The cruise industry has taken this approach to avoid paying US taxes.   Royal Caribbean is not an American company.  They don't own any US flagged ships.   They avoid paying substantial amounts of US taxes by registering the company in Liberia and their ships in the Bahamas.  Why should the US rewrite laws to benefit foreign corporations that don't pay US tax?  Just so less than 0.0001% of the US population can go on a cruise vacation they desire?  The number of people that want to take such a voyage is a small subset of the overall cruise industry.  It's a lot to ask when you consider that it impacts such a small group of cruisers such as "I want to cruise from Hawaii and stay on the ship for a B2B ending in Seattle".  That's maybe a couple hundred people per year.