The more requests you make, the harder it is for the room assigner. I advise that you pick your top priority and only request that. For example connecting, non-smoking. I agree with the above posts that Big Pine Key is your best choice and I would advise telling the resort that you have an older member in your party and you wish to be in Big Pine Key for a shorter walking distance. However, the room assigner will think that it is more important to be in Big Pine Key than it is to have connecting rooms which (I don't know) might cause a problem for you. There are lots of requests at the GF for connects and they may run out in Big Pine Key. Decide what is most important and request that first then say that you would "prefer" your second choice. That should minimize chances of being dissapointed. It's very hard for room assigners to meet every request because almost everyone at the GF has a special request. They are paying a lot and expect a lot because of it. Also, call the GF directly to make your requests 5 days or less before your arrival.