When should I cut bait on a recruit & move on to the next one?

I’m in my first season at a D2, and going after a recruit who has “very high” interest in a D prestige, sim-coached D1 school.

Do I have a chance to flip him, and if so what’s the best approach to using recruiting $ to do so?

It depends on where you’re at in the process. I definitely don’t recommend trying to come from zero to overwhelm a higher level sim who is already at VH and has a scholarship offer in the table. Certainly not unless you have a lot of experience with the system and know exactly what you’re doing, and where all your resources are going to be spent.

If you’ve been on this guy all along and have a good deal of AP invested in him as well (say you’re also at very high and have an offer on the table as well) then it’s probably worth it to make some PT promises, a start and 20 minutes is pretty standard - assuming you’re willing to keep them, and you should be if you’re willing to invest significant resources battling a D1 sim for him - and a CV, plus maybe 3-4 HVs. That should get you back well into the lead for most recruits, unless you have preference disadvantages. The goal is to get that sim down to very low, at which point they will give up. So if it gets them to low, probably another 2-3 HVs is enough. If it only gets them down to moderate, you’ll want to do a good bit more.

If you can’t or don’t want to spend a CV and up to 10 visits (possibly more if you’re not already at Very High) and keep those promises to him, then yes, cut him loose now.