Before I waste a bunch of money, I was hoping to get some good veteran advice. We just got through the very first cycle of recruiting and I went hard for a guy early. He's currently considering me (DIII) and a DII human coached school. The details are as follows:

ME: DIII, A+ prestige, 320 miles away

Other school: DII, D+ prestige, 80 miles away

1. Do I have any chance of winning this battle?

2. What would it take/cost to win?

3. Any suggestions for how to go about this?

I'd say your chances are not good. Is the D2 school considering other guys at that position? If so, you might have a chance, otherwise I would say go after your next choice.

With the distance advantage and the division advantage no chance if he puts any kind of money in.

check the coaches history. if hes not an experienced coach, i would definitely consider continuing the battle. i have won tons of battles from d3 to d2 so its definitely possible. the prestige advantage is small but he has more money per scholarship, so you will need to figure out how much he has to spend. also how much he seems to be spending elsewhere. overall you have to have pretty favorable conditions other than what you mentioned to have a chance. consider not spending any more until just before signings as well.