should i drop off a guy if he is a Late preference and im DII and 1 DI Sim team is on him. Or can i possibly beat them out since they wont sign until the second period.

Not enough information...what level are you both at currently on the player? Have you both been on the player for an equal amount of time or is there a chance the Sim is one or more turns ahead of you in AP investment? How far away is the player from you and how many other recruiting battles do you have that might consume resources for CV and HV's? Where is recruiting at? Is there a chance a human D1 team might come onto the player as a backup option if they get knocked off their primary target of an early Session 1 signing?

And don't forget preferences! If you have any Good or VG, then your chances are a ton better!