Depends on a variety of factors -- Send him one phone call or coach call to make sure he's even open to being recruited by you, but after that I would definitely not sink a dime in on him until the first Word on the Street report comes out. See how tight the D2 program is on the kid. If you get a message saying he's *very* tight, then it's time to move on. If it says that he's had some interest from (d2 school name) but is keeping his options open, then you're in better shape. You'll have to have FSS'd the recruit's state for this, but I assume you already have since you like the kid.
The next thing to look at is distance from your school to the recruit. The closer the kid is, the better because you'll be able to play the pulldown game for the cheapest amount of money possible. Heck, if he's super close (< 70) there's even a chance he'll be immediately recruitable even though he still shows on the D2 screen for you. Again, the feedback you get to a phone call will determine. The nice thing about battling a Sim is it's just a bidding war -- you have to buy more influence than the Sim has spent (and then pray nobody else is after the same guy), knowing that Sim won't spend any more (unless it drags to beyond the signing window...)
Last, assess how much cash you have and your other needs, how many walk-ons you're willing to take on if you try and fail, etc. Again, it's a bidding war so know how much you're willing to bid and/or how much you need to fill your need areas before you go stretching. You absolutely can pull down D2 guys and win the battle against Simmy. Its all a question of risk vs. reward.