Location is important for both your social life and professional life, therefore where you live has a direct impact on your happiness and success. For Gen-Y'ers, you really want to live in a city, where the action is. There are also the most jobs in a city.

Monica, love the post. I completely agree with your 4 points. I would like to add a 5th.

Here is an entrepreneur thought-leader podcasts:http://www.stanford.edu/group/edcorner/uploads/podcast/conwayMaples080123.mp3. The podcast interviews two Angel investors who literally say, "If you're not in Northern California, don't start a business." Now, I don't completely agree with them, but I have been to NorCal and have felt the difference (I'm in SoCal). Information moves faster, there are more investors and entrepreneurs, and everyone seems to want to help each other more. If you want to start an internet-based company, then I must side with them and advise you to move to Silicon Valley. That's my two cents :)

Monica -

I am prejudiced but you chose the best city in the country! Chicago has anything and everything you could want, no matter what your age. Growing up here was fantastic and living nearby keeps me in touch with everything important to me.

I'm glad you now call it home.