No, rooms get assigned 2-3 days out. Your best bet is to call the Main Reservations line and the phone CM will be able to change your requests to Upper Floor and Jamaica. This is one of the many reasons why I don't recommend making room requests via the Online Check In procedure. The options are predetermined, very limited and usually not what we like to request.
Not everyone that does Online Check In is able to Bypass The Front Desk. If you have completed Online Check In you will have 1 of the 3 Check In experiences:
1. Bypass The Front Desk - You will receive a text/email around the time you specify you will be arriving. The text/email will either say your room is ready and provide you room number along with a link to the resort map. Or if your room is not ready yet, your text/email will say this and then specify you will receive another text/email with your room number when it is ready. Once you receive either one of these texts, you are fully checked in to your resort and can go directly to the Parks if you want and use your tickets, dining credits, Memory Maker, etc.
2. Streamlined Check In - Once you arrive you will go to the Streamlined Check In Kiosk and show your ID. The CM will give you your paperwork and if your room is ready will give you your room number. If your room is not ready you will receive a text/email when it is ready with your room number. Once you leave the Streamlined Check In Kiosk you are fully checked in to your resort and can go directly to the Parks if you want and use your tickets, dining credits, Memory Maker, etc.
3. Regular Online Check In - Once you arrive you will go to the Online Check In Desk and show your ID. The CM will give you your paperwork and if your room is ready will give you your room number. If your room is not ready you will receive a text/email when it is ready with your room number. Once you leave the Online Check In Desk you are fully checked in to your resort and can go directly to the Parks if you want and use your tickets, dining credits, Memory Maker, etc.
Having said all that, some people who were first informed they were going to do the Streamlined Check In were later informed that they were now eligible for Bypass The Front Desk. So it could change, but might now.
Nobody, and I mean nobody, has been able to figure out how they determine who gets which check in experience. We were traveling with friends, both did online check in, both had the exact same packages, were on the same flight and on the same Magical Express Bus. We got to Bypass the Front Desk and our friends had Streamlined Check In.