If something is guaranteed that means you will get that thing, no question. And that is not the case when it comes to room types at WDW. They are not guaranteed no question. And they can only accommodate accordingly if they have something similar to hand out. And as I can attest to, that isn't always the case.
As far as connecting rooms go, if you have 2 adults they can give you 2 non-connecting rooms and have an adult sleep in each room. They have done so in the past, so to them that seems to them to be accommodating people accordingly--everyone has a place to sleep, and no child is left unattended.
But to say someone is guaranteed to get connecting rooms needs to come with an * after saying guaranteed as much as they can, which is not 100% guaranteed. And is misleading them at worst.
We're never really going to come onto even ground with this.
I really do understand what you're saying - it can't be guaranteed because it's not 100% that something won't happen. But that's life, right? There's always an off chance something might happen at some point in time.
Yes, 2 adults can get 2 rooms by putting 1 adult in each room and for most bookings with 2 rooms they book 2 reservations doing exactly that.
Guaranteeing connecting rooms is Disney's wording, not mine. If you'd rather say it's never guaranteed that's totally fine. But if Disney will guarantee me 2 connecting rooms why wouldn't I assume they would? If Disney has a policy stating such, why wouldn't I judge based off of the policy of the place I'm making arrangements with?
Of course anyone could say 'they guarantee connecting rooms for this set of people, but beware, a pipe could burst and you could be out of luck.' Or 'well, you booked a garden view room. They're nice, but you might get downgraded at check in because it does happen from time to time.'
If Disney is going to create a category of people that have a special booking procedure to ensure they get connecting rooms that's certainly what I'd expect. If for some reason something happened and they were unable to provide the rooms at that particular resort they'd put the family somewhere else that meets their needs. But since this board follows Disney policy, what's wrong with stating what Disney's policy is?
ETA: Twinboysmom - For kicks while I wait for my coffee I called reservations, said I'm a single mom with 5 kids and I'm planning a vacation. I asked if I could get 2 rooms at a value that were connecting since I don't fit in one room. She stuck me on hold to check on it and came back and advised the same... I could have 2 connecting rooms. I asked if they'd be guaranteed and she said yes.
For the record - I'm more of a person that says 'don't believe the reservation CMs' since they often get stuff wrong. But since you advised I should try booking in that fashion after our back and forth, I gave it a go. I guess you could always do the same and see what they say.