So back to a recruit, still not considering me after 30 calls, 10 letters, 2 HV, ST, and a scholarship

I honestly may come up empty in this recruiting season with 4 schollys

Were you attempting to pull down a D2 recruit or was he D3?  Where you trying to recruit over 360 miles away?  How many openings did the SIM have?

Yes to either of the first two questions I would recommend to go look elsewhere (especially for a first timer) and depending on how tight the recruit was the SIM, it still might be a losing proposition to battle him.

I was 200 miles away and he's d3, I also have a prestige advantage over the sim. I only have $1000 in my budget

Well the SIM also recruits at 200 miles regardless of distance and D3 prestige isn't large between letter grades so it'll just come down to who spends more money on him.  Best guess without knowing FSS, I'd say SIM has spent at least 2K+ (more than likely 3K+) depending on whether he's their primary target or not (more if they have playoff cash).  

The problem is that my recruit is not even CONSIDERING yet

If you only have $1K left and he's not considering you yet, you are definitely better off looking elsewhere for a recruit not considering anyone else.  Even if spending that $1K got you on the list, it probably won't be enough to win you the recruit unless that 1K more than doubles the effort you've already put in.

Now I have 2 considering me, 1 is amongs another school, so I'll have to wait for the word on the street, I should get 1 out of 4 scholarships full, let's see if I can get 2