This is something I have trouble understanding. How is it in this day and age Disney can't guarantee connecting rooms? I can book a Hilton and through their app I can not only get guaranteed connecting rooms I can look at a floor map and pick my exact room. I've been tempted to book connecting rooms for us but tried it once at AoA, got burned so never again. We vacation to spend time together, not apart. Hopefully Disney can work this out someday.
It's not that they can't, it's that they choose not to.
I actually feel Disney doesn't give/guarantee connecting rooms as a way to get you to pay extra for family suites and such.
We are a family of six who goes to Disney every other yr. (at least) and often times with another family/parents.
Only once have we had rooms "close" and that was at CR where we were two rooms apart and on op sides of the hall.
Every other time we have been separated, sometimes by completely different sections of the resort.
Last time I actually asked if there was anything closer and low and behold they had rooms closer to each other. (Hats off to that cm for taking time to look)
So this yr. to give you numbers and why it's in Disneys interest to not connect families...
AOA, one suite, $53xx. (I need two and a regular room too)
POR, one preferred room, $1784 (I need three rooms)
POR, one garden view room w/special discount, $1391 (need three)
As you can see, even just needing two rooms for my family alone, in order to guarantee all six of us being together it is more then double POR. They know most families don't want to be or can't be separated so it "forces" them to pay more by not guaranteeing connecting rooms.
In fairness, I know many people have got connecting rooms but for us to never get them out of all the times we travel it seems odd. It is also funny to me how many CMs will quote you as getting connecting rooms as a guarantee when that's clearly not the case or the policy. (Had to laugh when I was told this time around we were guaranteed connecting because we have more kids then adults)
I have never been to any other resort or hotel in general that doesn't give you connecting rooms. I feel it's laziness on Disneys part and a gimmick to get more money out of you.
As for the numbers above and advise of two values being the best option, in many cases yes but since mods get higher discounts you can often stay there for the same, close to, or less so investigate all options