For D2 looking at challenging D1 squads for D1 players in RS2, the first thing to look at is signing preference. If they are early or end of period 1 recruits, you need to be very careful before you offer visits. A D1 school can come in fast and take them with relatively little effort, and you’ll lose what you invest. The exception is when you can correctly assess that the D1 school does not want the recruit enough to invest visits, or will not be able to do so. So use caution with visits on players up in division in the first session, if they want to sign in the first session.
If you’re in the second session, and the player has the first session tendency, and the D1 school is still at low or very low, you are likely in decent shape. If they could have or wanted to spend enough to take the recruit from you, they would have done so already. The exception here is if you’re looking at a team who has lost a player and gained scholarship resources, like early entry or they cut a sim signed player. You can look through their roster, and their conference news to check for that kind of thing.
If the player is a late signee, now is the battle. You’re basically going to have to decide which player is more likely to draw more fire. You can look at the needs of your challengers, look at how many openings they have vs who they’ve already signed. There’s early no silver bullet approach in this situation, because you can’t say for sure what the other coaches are thinking or planning, or what they have left. The best you can do is make a good guess. If I’ve already spent on a RS2 guy in the first session in your position, and I determine that a D1 opponent still has juice left to go for him in RS2, I would be hesitant to split my resources.
If these are late signing guys, the safest play may be to wait a cycle and see what happens, let your opponents lay down first. While there is a chance one or both might sign on the first cycle, it’s more likely that they will give you 2-3 cycles to figure it all out. There’s risk all the way around, you just need to decide where your value play is.