#1. Kid is being considered by a Sim D Prestige D2 school. My team is a C- D3. He told me I am a back-up option, and scouting reports say that I only have a shot if the "big boys pass on him". Is there any chance I can get this guy? If so, how much effort would I need to give?

#2. Kid is a high D2 recruit. He doesn't return phone calls, and scouting reports say that I have no chance to get him. Currently he is not considering anyone. Does this mean that I legitimately have no chance, or does it mean that I would just need to put quite a bit of effort in order to get him?

#2 you have no chance.
 
#1 needs to be pulled down. What does FSS say about the sim - is the kid a high priority or a low priority? If high, it will take a lot of evals to pull him down. If low, it can be easier, but not necessarily cheap.

Best advice, find different recruits.

You wasted money scouting #2.  If they don't answer your call don't spend money on them.

I would only attempt #1 if he was extremely close to my campus and the FSS Word on the Street made it clear that the Sim had only done the bare minimum to be considered. If he's "definitely leaning" or "tight," I walk without spending another dime. I'm not sure how much extra effort you need to pour in to overcome the D2 D vs. D3 C- prestige factor, but I would be expecting to put a significant chunk of my bankroll into the effort if I decided to pull the trigger, and he'd have to have ungodly potentials and starting values in the cores to get me to make that decision.