Direct-to-room check-in is determined by Disney. If you're eligible (you have to provide your arrival time; enter a credit card for room charges; have received your magic bands; and provide a cell phone number and/or e-mail address during online check-in to be eligible), you'll get a text or e-mail from Disney on your arrival day letting you know you can go straight to your room. I got an e-mail shortly after (within a day or so) doing our online check in letting me know we *might* be able to go straight to our room upon arrival. I always start stalking my phone for messages about an hour before our scheduled arrival time.
It never hurts to ask (nicely) to be moved to a different room location if you're not happy with your original assignment. I've asked to have my room location changed on two different visits because the rooms we were originally assigned weren't really what we asked for. One time was a suite at AoA and the other time was connecting rooms at Pop Century. At Pop, we had been assigned rooms in Building 2 of the 50's section. They were literally the same connecting rooms we had stayed in on the last trip. I nicely asked if they had any other connecting rooms available. They were able to move us to Building 9 in the 80's. The only drawback was that only 1 of the connecting rooms was ready at that time. We weren't going to be able to get in to the other one until later that day. That wasn't a problem for us -- we just unloaded everything from the car and put it in the room that was available and moved the stuff into the other room when we got back from the park later that night. If you're flexible, they really try to accommodate your requests.
