I've read many of these threads over the years, and the majority of people always say it doesn't matter. However, and I have no scientific evidence to back this up, I think it has to. If you get there at 8 AM and ask if you were assigned room "x" (or location x, or longhouse x, or whatever), and they say no, they are able to check to see if another room is available that they could move you to (even if it means you waiting much longer to get into the room). However, if you arrive at 11:00 PM, the only rooms left unoccupied will be rooms that aren't booked for the night, because pretty much everyone has already arrived and gotten into their room. So while they can still see about moving you to a location you like better, they won't be much left. The advent of online check in and going straight to the room makes this somewhat harder, since once they text a room number to someone they cannot reassign that room to you, even though the person getting it might not arrive until much later than you. However, not everyone uses online checkin, so if they haven't let someone know what room they were assigned to they could change the assignment, give it to you at 8:00 AM, and assign them a different room.
It's been a while, but I know this happened to us back before online check in. We travelled with my parents. They arrived earlier than us and asked about our room location. They obviously couldn't tell them our exact room number but did say it was near them. When we arrived we were nowhere near their room,and when we asked it turned out our room has been reassigned before we arrived and checked in. But on the other hand, when I was growing up we always drove over and checked in super early after staying offsite the first night, and they were always able to pull up available rooms at POR and show us our choices if we wanted a different building, etc.
I agree with everyone that which room isn't going to make or break your vacation, but i actually feel like a great location and view can really enhance the vacation (I'm talking mostly deluxes when it comes to view, location applies to any resort). So If I can try to get it, I'm going to. My success rate is maybe 50/50 if I want something specific, but I at least want to ask.