Well Trump is a resident of NYC, which is located in a heavy blue district, and he was one of the most depised figures in New York even before getting into politics. So fat chance of him winning a house election, and its rare for some who has no congressional experience to be chosen as speaker.
I suppose he could move to florida officially, but he would have to wait to run, because they have a requirement that a candidate be a resident for a certain number of years , and no he isnt considered a resident just because he owns property and stays there alot. He also wouldnt likely change residency to begin with since he gets several tax benefits for his business as a resident of New York that arent available for non-residents