So we are avid campers, so packing light for all types of weather and living in small spaces will be no issue for us.
But I have questions around things like dining and the shows.
Kari
Hope I can help. Maybe some others have more recent insight into the workings, as our last
Disney cruise was in 2009.
"We have second seating for dinner. I think my kids will be fine with the late time, but I'm curious - how long does dinner service tend to take?
-- At least an hour, maybe 90 minutes.
Also how many other guests do you tend to sit with?
--Depends on the table you have requested. The tables range from 4-8 people, although there are a few 2-tops and a few larger tables.
"I've read that many parents send their kids to the play areas"
-- Once your kids get a taste of the club, they will be gone. I think there is an eat and play option where you get the kids food quickly and then the staff takes them to club in the middle of dinner.
"Since I'm a single parent that would leave me sitting by myself which is okay if there are other friendly table guests."
-- Lots of friendly people on the ship. Depends on that table size how many people will be with you.
"Since we have second seating for dinner, would we watch shows before dinner?"
--Yes, although if you go to a different meal, like Palo, you could catch either show time.
Also, I assume room service food is all included? (besides tipping).
-- Most food is included in the price. There are some things on the menu and at stations around the ship that are not. Popcorn and candy outside the show, for instance, cost extra. Canned pop and bottled water are extra. All of this goes on your room tab. As far as tipping goes, it is your preference, but we bring along a stack of singles. We have a minimum tip of a couple bucks, and then use a tip-per-plate strategy for larger orders. Our kids really like the room service, and do snacks and a movie most nights.
Approximately how much cash should one take on the trip for tipping, expenses not covered, etc? Is there a way to get more cash if needed?
-- The only CASH thing I can think of on the ship is Room Service tips. Everything else can go on the room charge, now even the staff tips can. St. Somewhere just told me that room service tips can go on the card too. If you mean all expenses and are not planning on using a credit card, then the list of charges is long and distinguished. We can answer that depending on your expansion.
I think I read cell phones are not permitted on the boat, so I assume they have phones for calling home but are they expensive?
-- Cell phones are permitted on the boat. You will have to pay through the teeth, one arm, and your eldest child to cover the cost. You can also use the in-room phone to call. You will have to check on the cost, but I think it is in the $10's per minute to do it. FAR better off to use a pay phone in port with an international calling card. Not thinking you will pick up a Canadian cell tower in Alaska, but many of the excursions go into Canada, so you may be able to time your calls for when you are in "local roaming" instead of on the ship, or in US territory.
and pay for the convenience of my data plan when I am not. 
