Welcome to HAL! I am sure you will have an amazing cruise. To answer a few from my perspective:
Lots of great options! Depends a bit on the ship, but on the Nieuw Amsterdam we really enjoyed the Pinnacle Bar which was usually quiet during the day. Nice sea views. Most of the bars are available to sit in even if they are closed/not in use - the Gallery bar behind the casino is also quiet during the day though no ocean views. Along deck 2 & 3 there are some nice sitting areas also. We also enjoyed sitting by the guest services desk on deck 1 in the atrium. Lots of people coming and going for people watching. NA also has had the Crow's Next conversion to EXC Central so it has nice seating areas as well as a bar/coffee shop.
If you want a private area one thing to consider is a cabana rental. For a 14 day I think a cabana for 2 is $400-600 depending if you go with the Lido or Retreat. They offer in cabana service during the day. I am doing my first one next month but have read a lot of great reviews. There is also a larger family cabana for up to 4 people.
All of our recent cruises have been in a Neptune suite so it has been included for us. They do a pretty good job on the laundry. I don't believe any of the ships have a laundromat available. The package is probably the best deal but I will leave others to comment on this.
100% yes. Absolutely no issue. The couple at the table next to us ordered every single appetizer on the menu each night. I will often have the pasta as a starter. Some nights we order 3 deserts for the 2 of us. Do not be shy about asking for what you want. The crew on HAL is fantastic across the board.
You did not ask, but we have a strong preference for fixed seating. You absolutely get better and more personalized service having the same waiter & assistant waiter each night.
Sea days only. If you have a late arrival into port they may serve a limited menu (I have only seen this once with a 1 PM arrival into Juneau).
I can only speak to Sitka - you absolutely MUST see the Raptor Center and the Fortress of the Bear. Both are Fantastic. These are combined with either a boat tour looking for sea otters, or a visit to a Salmon Hatchery. If you have never seen a hatchery or a fish ladder this is interesting, but I would not do that again. The "Best of Sitka: Otters, Raptors & Bears always gets rave reviews.
I agree it is all about attitude. Over the years HAL has shifted from a more "premium" line to more mainstream. Those of us who have sailed for years (and folks who have been sailing with HAL for many years) remember how it used to be and do not appreciate the various downgrades over the years. A recent example is the addition of the "indulge" option in the Main Dining Room allows you to buy the steak and lobster every night, but you can no longer get lobster for free anywhere onboard - the surf & turf on the gala night is now steak and shrimp instead.
Another example is the onboard entertainment. They used to do more of a broadway style show with singing and dancing. This has been replaced with the "Step One Dance Company" which is not everyone's cup of tea. The crowd on HAL tends to skew older but the music for this was mostly from the last 20 years. A couple nights the main "entertainment" was either a movie, or they also have a nature documentary with live music being played. For those of us who sail frequently these get a bit old - how many times can you watch the same documentary before it gets old? Not many!
I agree completely with @cbr663 two points - HAL can be very inconsistent. Your cruise experience will vary greatly from that of the people in the cabin next door. Expectations also play a large role. The billing errors can be very tedious. I always keep a close eye on my account and always report errors right away. We are fortunate to have access to the Neptune Lounge and they always sort things out right away.
Across the board, the front desk/guest services department is either the least helpful one. It is totally mind boggling as the crew everywhere are so accommodating and then when you get to the front desk they either lack the authority or ability or willingness to fix your issue. Even the managers seem to be unable to help. This has been going on for years and across every ship I have ever gone to the front desk.
Now, all that being said - we love HAL. They are our favorite cruise line. The sailing we did in August was the best cruise we have ever done - despite all the changes and restrictions.
They have added a number of EXC talks to their cruises - these were all 30-40 minute presentations on various topics (such as the Iditarod trail, pioneering women of Alaska, 150 year history of HAL, whales, etc). These were absolutely fantastic! They also have added the Music Walk to most of their ships. Depending on your taste in music these are great. BB King's was very popular and played a nice selection of mostly 50s-70s. Very full every night with lots of folks out on the dance floor dancing.
The Lido is great - really nice selection and great food. The MDR menus are more limited than they once were (I forgive this due to the supply chain issues, we will see what happens as time goes on). The food in the MDR was still good though & there was still chicken, fish & steak available nightly. Also the specialty dining venues are all very good.
It is important to remember that HAL is a pretty traditional cruise. There are no waterslides, ice skating rinks, go cart tracks, etc. The passenger ages skew older. The night life is limited. Many of the negative reviews I have read are people who never should have been on HAL in the first place and would have been much happier somewhere else. We hated Carnival and NCL but there was nothing wrong with the brands, it was just not the right cruise line for us & there is nothing wrong with that!
If you have some time there is a link to my live from thread that I did on the Nieuw Amsterdam in August. I posted a lot of detail including daily programs and menus & meal pictures. Otherwise feel free to ask us any of your questions.