Test ride a lot and talk to the bike shop people extensively. There is such a huge difference in what they know and how they treat you.

Don't buy used unless you have a very good idea of geometry and fit - I unfortunately did that with my first bike and my shoulder pain from being stretched out doesn't show up until 30 minutes into the ride.

I'll tell you next week how my hopefully "perfect" cyclocross bike feels (Specialized Crux). I did test ride the Specialized Tricross and it was not a comfortable ride. It was also a lot of work for me to get up to my usual speed. The Giant TCX W that I tested was very smooth and fast, but a shade too big and too expensive for me.

Pretty much nowhere else had a cross bike in my size to test or even any bike in my size.

Northern Michigan? If you have time, maybe a nice trip down to Grand Rapids, Ann Arbor, or Detroit for more choices.