Transfer Portal I would say some of that comes down to how good the player is. Fringe guy looking for more playing time is different from a redshirt freshman QB who just helped lead you to the FCS quarterfinals.
As for Pinnick going to Colorado, let's wait to see how things play out before jumping to conclusions. If he goes to Colorado, then it's either they offered him the most money and/or it's the highest profile FBS team he got an offer from. But this could just be the first visit of a few and he's seeing what's out there. I'm sure there are other more stable FBS programs who can offer him money as well to play.