Upgrades within the resorts themselves are rare and upgrades from resort to resort are even rarer. Generally the only reason why you would be upgraded is if the room category you initially booked was overbooked and they have availability in a higher room category. Sometimes when there is a lot of availability CMs can upgrade you within the hotel to a nicer room for a lower price than usual or even for free, but that rarely happens. The only way they would upgrade you to a different resort level is if every room in your original hotel and every room in your resort category is full at the time of check-in. They will never bump you up to a nicer hotel for no reason or even for a small fee. When people get upgrades, 99% of the time it is not just because Disney decides to give it to them just because they want to be nice. There is almost always a reason to upgrade someone that benefits Disney. To some extent there is luck involved in the sense that when Disney needs to upgrade people there might not be a noticeable reason why a certain party received the upgrade over another, but Disney almost always has a reason for offering the upgrade in the first place.
Since you are going in October when the hotels are not likely to be full the chances of being upgraded to a higher resort category are pretty much non-existent. You may be able to snag a preferred room at ASMo when you check-in (I would innocently ask about a particular building that you know is preferred), but it is highly unlikely because they probably will have plenty of room in your original category.
If you don't get an upgrade, don't see it as not getting your money's worth. Staying with the room type and resort you paid for is just that, you get what you paid for. If you want a nicer room at your resort or moderate/deluxe, I highly reccomend that you change your reservation before you go. Don't pay less assuming that you will get the upgrade, because 9 times out of 10, you won't.