Few answers that I know of!
medicals are now generally conducted in Manchester & London as the sports science facilities are outstanding compared to anywhere else. The days of going local are long gone as they don’t have the equipment.
4 medical at once! Can’t see that happening. A medical is now often a full day, this would be an appointment as above then driven back to Sheffield for a fitness test and the player would generally meet the manager at this stage along with his agent.
contracts are generally ongoing and even after the medical there will be major decisions to be made. Image rights, pay, loyalty bonus, signing on fees and the biggest one (agents fees) and whose paying them.
Always makes me laugh when people say it’s a Free Transfer. There is no such thing as a free transfer anymore. The fee now goes to the agent. Pay him/her what they want and you get your man, hesitate and they go to the club that will without a moments hesitation.