One thing to be aware of is that players respond to recruiting efforts in the order they get them. For example, say you and another coach both sent calls, letters, and 2 evals but the other coach also made a scholarship offer and sent a couple of HVs. If the player got your responses first, he might say you were a backup but then consider the other school after getting their offers. I once had a player tell me that he was really struggling between my school and another school but he signed with me the same cycle.
As far as where you are right now, the real key is do you have enough cash, prestige, distance advantage to beat the school he is considering? I would probably look elsewhere but it's your call.