I should clarify that both the Food4Rhino installer and the single-click Pollination Grasshopper Installer are FREE. We announced that the Pollination Grasshopper installer is “forever free” in January.
The only difference is that, for one, you have to make a Food4Rhino account and, for the other, you have to make a Pollination account. And, the Pollination single-click installer is currently Windows-only as I mentioned.
So this means that it’s not clear which one you are referring to when you say “the free installer.” I also can’t really tell which one “makes it smoother” since, if everyone is using Windows, the single-click installer is definitely going to be smoother. I imagine that you have Mac users among your students, though, so I guess you’re probably going with the Food4Rhino route.