Wow, I think you'd get extra-special double cool commuting points for having to cross into another state on your commute!

What I would do in your case is to just try it. Try it on one route one day and the other route the other day and just see how it goes. Or if you're nervous about taking on the whole commute in one day, drive in with your bike in your car and ride home on one route, then the next day ride into work on your bike and drive home. This kind of hybrid commute is an approach that I think a lot of people take on a routine basis, especially if they have a long or difficult commute. I'd be more inclined to take the slightly farther but less busy road. You'll get good at the hills in pretty short order. A year ago I was asking on here about dealing with hills on my commute (I don't really have any truly flat sections, and the first 6 miles (or last, depending on the time of day) is pretty much 3 miles down then three miles back up) and while I would like to say that now I'm so used to them that I hardly notice them, the truth is I STILL hate them, but they are much, much easier. I had to walk them the first few times and I always tell myself that that's still an option (as is stopping at the coffee shop at the base of the three mile hill and calling DH for a ride! I've never done it, but I've been tempted.).

Good luck!

Sarah