Just back from our first stay at POR and enjoyed it quite a bit! Thought I'd share my experience on a few things, including results with room requests and an attempted early check in. I spent quite a lot of time on PortOrleans.org and the Touring Plans website looking at pictures, maps, room views, etc.. Not to mention reading posts here. I settled on my ideal area and requests and tried to keep it fairly simple while giving some sample room numbers in Acadian House on my TP room request. On the online check-in, I gave a 12:30 pm arrival and asked to prioritize a ready room over other requests. I got a text at maybe 11-11:30 that our room wasn't ready yet and they'd keep us posted. Nothing more after that. I think we arrived around 1:15-1:30, checked in, and nothing was ready at that point. They were having some computer issues and there seemed to be quite a few people waiting around, though I'm not sure how many were just checking in. We waited maybe 45 minutes while trying to decide if we should store our luggage and head to Animal Kingdom. I double checked on room status and the very helpful CM managed to get us into a room in Magnolia Terrace. It wasn't much of what we requested besides Mansions and somewhat close to transportation, but ended up working out just fine anyway, and it was definitely better that we got the room considering how exhausted we were by the time we got back that night. The room was very quiet and comfortable.
We had a rental car, but took the bus to Magic Kingdom and one evening to Hollywood Studios. We used the East bus stop, and through some miracle, 4 out of 5 times our bus was arriving at the same time we did. The 5th time we waited probably 15 minutes, and then got stuck in horrible traffic on the way to MK, but that seemed to be an anomaly. Most of the times, buses were pretty packed, but usually at least 1-2 of us got seats. I saw several cases where people gave up seats to those who needed them (small kids, seniors). And then some buses were quite empty. Coming back was good for the most part, but we did wait for a 3rd bus coming back from DHS after the Star Wars show (and a leisurely exit to avoid crowds). It still wasn't a terribly long time though, considering. The sign at the bus stop only seemed to ever show times for 2-3 of the places, and not ever where I was going, so those weren't helpful at all. Not that I really needed them as I was running to the bus.
Overall, we spent more time at the parks than the resort, and sadly never even made it to the pools, but definitely liked POR and would consider it as option again in the future. Thanks to all of you who've shared helpful info here!
