would it even be possible? In the case I am looking at I'm not going to do it becauseof distance, but can it even be done?  I'm a A+ prestige and the DI is a D    

I think it would be extremely difficult, and most likely impossible if the FSS says 'very tight' or anything like that.

Yes it can be done.  a few seasons back morganballer stole this guy from 3 D1 schools, including at least 1 big 6 conference team.  i don't know what the other teams spent, but i had put in like 16k as a D prestige at the time.

http://whatifsports.com/hd/PlayerProfile/Ratings.aspx?tid=0&pid=1809467

so if it can be done against 3 human coaches, it can be done against 1 sim.

Used to do it all the time.  It's very possible.

all the time. very possible. although, watch out for "very tight". if you are not local, and you see very tight, you have no chance (roughly). also, if you see very tight, and the sim is like d+ or c-, you are really going to have to spend a lot. 

i basically think you can easily win 90% of your battles up a division vs sims (regardless of d3vd2 or d2vd1). but, you have to pick em carefully. for d1, that basically means i won't battle a sim who has a player on very tight. pretty much never - but not absolutely. if you look at the sims scholarships and who he is after, and see its probably a low very tight, and the player is local, you can do it. but its still costly. i basically recommend for newer coaches, don't do it. but for not very tight, its surprisingly easy to win - almost regardless of prestige. hard not very tights can be tough so prestige is definitely a factor, but even a c- sims last target is pretty easy to pluck away.