The recruit is very close. I'm DIII A+, Sim is DII C+. I've dumped a bunch of money on him from the beginning to pull him down. A couple of cycles ago he started accepting home visits but at the same time the DII Sim team became "*very* tight" with him. We are 2 cycles into the signing period and he is still unsigned. I have sent him a few home visits but I have never been on his "considering" list. My question is, is this a winnable battle and how much do you think it will take to win?

How many open scholarships do YOU have?
I think you have a decent possibility of being disappointed ...

It sounds like you've done just enough to keep him from signing immediately with the sim school, but not enough to actually be considered, and without that you won't get him to sign with you.

I had a B prestige before in DIII and i was going for a guy, i ran out of money and a DII sim got on his considering list. But at the end of recruiting, he signed with me rather than the Sim.

You need to put in double of what you have put in to have a chance at signing the guy. For example, if you had put in 20HV so far, you probably need another 20.

I think the minimum threshhold for very tight is the equivalent of 30 HV.  Can you beat that put the prestige multiplier?   It will be expensive.   Odds are you can find another chlub with some more scouting...

I gave up on the guy late last night, and have just sent him a couple PT promises that have been turned down since. He still has not signed and is now "definitely leaning towards X, but sources tell us he's not 100% sold." Any interpretation on whether I can win this guy? I'm still not on his considering list.

I would check for other options to see if there something comparable or better. If I find none, and that player is worth it, you can dump everything you have left on him and hope for the best. You have to be willing to take a walk-on if it fails. I see you signed all your other recruits so going all in is not a big deal.