Hey a fellow Manitoba Disney nut!
I saw you made a post on the POR thread and noticed that you were from MB then I saw that you had a PTR going on. I read the entire thing while watching the Jets at NJ (what a heartbreaker of a game). Mt DD(16) and I went on our first trip ever last August and our going on our second trip next August.
I think that you are making some incredible magical plans for your trip. I hope you don't mind me giving you a tip or two.
In reguards to photo pass be sure to get some pictures taken of just your kids, just you, single pictures of your kids etc. I found that the photo pass CMs were great but they seem to only want to take pictures of the whole family. This can get a tad boring when every picture is of the same four people.
We stayed at POR with the free dining and loved it! We used Disney trasportaion for the entire trip and did not have one issue. Sure the odd time we had to stand but this was not a big deal at all the trips are not all that long. If you stay at a Mod you would get the DDP plan free not the QSDP so that would save a bit of $ and lessen the price diff. Plus if you stay at AB one of your kids could use the truddle bed the other two could share a queen and you could have a queen all to yourself.
If you plan on going to one park a day why are you paying for a park hopper pass? You would be better off canceling the park hopper and getting a water, fun and more pass. Then on your first day you could go to Disney Quest when you go to DTD I'm sure your kids would have a ball. On your extra days go to TL and BB. Being a Canadian in October you would have the water parks to yourself

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I'm sure you have some ADRs you are thinking about. Our favorites by far were Chef Mickeys for breakfast and the Chrystal Palace for dinner. In fact they are the only two places we plan to revisit on our next trip. Another must do is Yee Haa Bob at POR it's free to get in all you have to do is order something. DD had a coke and I had a coffee tables are first come first serve and fill up quickly but people come and go threw out the night. We were lucky when we just got there a family of four just left and a couple from NFLD sat down. I just asked if we could join them and had the time of our lives!
The service that Disney offers by sending items to your resort is fantastic! They say to allow 48 hours but none of my parcels took that long and every night when I got "home" we had a voice mail letting me know that my parcels have arrived. The only thing was my DD and I were the type that left well befor the parks opened and came back after the cleaners kicked us out of the parks so we could not pick up anything becuse they were always closed when we were at the resort. Finely after a day at one of the water parks (they close earlier) were we able to go to the resort gift shop. The kicker was just about everything that we bought was available at the resort gift shop

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I hope I didn't overstep my bounds here and if I did I'm sorry I'm only trying to help. This also is alot longer then I planed and for that I am also sorry. If you have any questions post them in your PTR and I'll be happy to help you out if I can and heck if I can't I'm sure someone else will.