So I figured out the commute is just a bit under 7 miles. The hills aren't anything steep just mellow incline and declines, nothing to be fussed over. I live in the city now so there isn't too much outside of concrete. A nice, quick ride would definitely be preferable.
I'm thinking this...
http://newyork.craigslist.org/mnh/bik/5413647461.html Only cause of budgetary reasons.
It may just be the name association with the Taj but I can't help but want it. I'd get a Weekender but I can't really justify spending over a grand for a bike again. Which I'm sure negates more or less all the options on the post above me.