We just did two connecting rooms at POR in May. We had 7 adults and 1 teenager (who wanted to sleep on the pull down!). Originally, we had 9 people but 1 had to drop out last minute. We got connecting rooms with no trouble even though they were pretty full the week we were there.
If you do POR, when you make your reservation, either call or call after making it online, and have them note you want "connecting" rooms. Have them specifically note how many young children you have under 10 also. I checked into the resort early (8am) and our connecting rooms were already set up in the system.
For what its worth, connecting rooms were probably the only part of our reservation we did not have issues with! In the end they had to cancel our reservation halfway through and then rebook it (kept us in same rooms and everything though) and covered breakfast for 9 at the Captains Grill. So in the end, we were happy with the resort.