I think this is the part that gets past most people in the heat of the moment. In most programs the position coach recommends the offer to the coordinator. If he signs off, final say goes to the HC. The commitability (this isn't a real word) of that offer then depends on the head coach along with the final numbers in the end come December and February.
As far as Bowen goes, I have a really hard time putting that on O'Leary or anyone else on the staff. He'd had one foot out the door for so long, you saw how it was all handled when Bowen made his announcement, the soccer player girlfriend with OU, etc. Time is going to tell on that one, and if he turns out to be a first round draft pick, so be it.
O'Leary is a very young dude early in his coaching career and he's got a pretty high profile gig. Need to see more of what he can do.
I think you absolutely have to pound the pavement in your territory and at your position though. You have to love it and have a passion for it. Having seen it at the I-AA level 20 years ago, there is absolutely no choice regardless of the level you are at and especially today with so many other things going on at the P5 level. Those I-AA guys don't have the money and resources the big schools do, and they can barely chase two star guys. You're turning over every rock trying to find players. All those guys I was with are now P5 coaches in their late forties and early 50s. They got there by being recruiters. Might be O'Leary's path in the end. Certainly was part of Freeman's.