Certainty, or Ambition?

I've got a few things to look at in the coming up weeks. I'll want to pick out a couple courses for certain, though we've got two strong competitors already, and then get registered for the fall. They're both 8-week so they should only take half the fall- but probably the latter half of it. So this is a grand opportunity. If I can convince them to fund me, I can move down, get set up, moved in, and have myself settled for work all before the books have to come down for me to get ready for my classes. The question is though, should I take one class, or two? Easier ones, or harder? Regardless, I'd like them to take chunks out of what I'll need to graduate. Any headstart will be fantastic.

But is it better to get hard things out of the way, really prove it all?

Or to look at the tight situation and setbacks, and look for what to do to make sure things can't go wrong?