Thanks for the great advice folks. The idea of driving and parking part way at first is great. There's a town 5 or so miles into the trip that would be a good spot to start from, plus it would eliminate one big hill. I think that's wise advice and I'll probably follow it.

Regarding my job, I'm a desk jockey. I sit on my ever-expanding ass every day drinking coffee. No problem relaxing after the morning commute in.

And yes, my bike is decked out with lights and the necessary commuting stuff, I know how to fix a flat and carry what I need for it, along with other tools and goodies.

Thanks again everybody.