I had all of these same questions and more and quizzed several CMs about the plan before finally booking it for our trip.
Aristomommy - I had most of the same concerns you do.
Can we have the MYW package only for one 4 nights stay or does it have to be for all 8 nights?
I was told that you can shorten your plan rather than have it for length of stay but that everyone in your room has to be on the same plan. For example, my agent gave me the choice of 3-night or 6-night for our 6-night/7-day stay. The only thing is that you can only do the plan for the number of nights you are staying regardless of the number of days.
Can DH use his "points" at a meal and I would share some of the meal with him. (for example share appetizer and dessert but get my own entree).
It's only myself and DH going on our trip and there is no way we can both eat an appetizer, entree and dessert. I asked if we could use one "sit-down" meal option and purchase an additional entree and was told by multiple CMs that there is no problem with that. You will need to tell the server
when you order that you wish to do it that way or they will have issues.
Also, do you keep track of the points yourself or can you get an update throughout the trip?
Apparently, your point balance prints at the bottom of every receipt you receive when you use your dining plan. You can also ask for a report from Guest Services at your resort at any time. When you check in, all of the credits for all three of you are pooled together and placed on your "Key to the World" card. You should be able to spend them however you see fit from that point. For example, your DD gets sit-down meals also. It would probably be cheaper for you guys to use her sit-down meal options for one of you and pay for her meal because she most likely doesn't each much anyway. If we had young kids, we would probably be doing it that way also.
The MYW + Dining will end up working out to a good deal for us. I am saving our points by only using 1 per regular sit-down so we can do some signatures like Jiko. We are also planning to use 4 of our meals for the Spirit of Aloha show. After I use 2 for Jiko and DH orders his own entree and we do Spirit of Aloha, we will still have 6 more sit-down meals to spend.
Even though I haven't been yet, I would still recommend + Dining. It sounds like it will be a fabulous $$ saver, especially if you use your credits wisely!
What are the best values at WDW with this plan? (if you can, please give $ amounts saved)
I would love to hear a response to this as well. Also, which Counter-Services are the best? Did anyone try resort-hopping for counter-service meals?