I think it's perfectly possible for it to be a difficult question. He wants two things--the job and you. That doesn't mean you're an "obligation"--it means he wants you.
In "ripping off the bandaid" and "letting him go" you are also, in a sense, rejecting him. Telling him that you don't want the hassle that goes with trying to make this work. Now, maybe you would rather lose him than go through the hassle, but it certainly doesn't sound that way to me.
It seems ridiculous not to even attempt it. If it doesn't work out, you can reassess. Or he can. Or both of you. Try to take "what's best for him" out of your thinking. Let HIM worry about what's best for him. If he does that, and you think about what's best for YOU, you can sit down and discuss it.
Otherwise, this will be like an O. Henry story, with each of you sacrificing for the other's sake and ultimately winding up with something that isn't great for either one of you.