A 14-50 outlet is supposed to be on a dedicated circuit, but I think the code wording is a little flexible about how that is set up. If you can prove/arrange/convince the inspector that you will only be using one outlet at a time, then that might be OK. A transfer switch that enables only one of the outlets at a time should make it pretty bulletproof for inspection. I do have a friend, though, who has two Teslas with the two outlets on a circuit as you propose. They have one car set to charge immediately when plugged in, and the other set to charge very late at night, so their timing is kept separate.
I might recommend that before even starting the work, you get in contact with your local inspector first to discuss what you want to do to see what he or she would require to pass it. Then, you wouldn’t have to change or redo something you have already put in.