Went to one of the local bike shops last night.
Eric’s Bikes of Madison. They carry mostly Specialized bikes. The salesman was very helpful.
Started on a Specialized Pitch:

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I liked it quite a bit, very light/responsive and comfortable.
Then he put me on a Sirrus:

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With some better tires I think this could be a great contender. It fit perfectly, was comfortable, and felt amazing.
Just had my phone, so you get potato today. This weekend we plan on going to the other bike shops in Madison to check out more options. Giant has an entry level model that looks enticing, so I want to check one of those out, otherwise we’ll see what pops.
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Thanks to everyone on the advice and info, it’s greatly appreciated.