I wouldn't worry so much about the hills (there aren't any that I can think of on that route) so much as the bridges. On a windy day, they're not going to be fun. At all.
Also, riding in rush out downtown traffic is probably going to be unpleasant. But I'm sure you've considered that.
I like the idea of easing into it, but I hope you've got stronger willpower than I do. The temptation to sleep the extra hour and just drive in is gonna be strong.