Clarkx3. There is actually only one high school in Cookeville and it has won a number of awards:
http://www.cookevillecavaliers.com/ As far as safety is concerned, any of the rentals in your price range are going to be in good neighborhoods. To be honest, there aren't too many bad neighborhoods. There really isn't a best "side" of town. Nice areas are scattered all over the place both within and outside the city limits. This has some good info:
http://en.wikipedia.org/wiki/Cookeville,_Tennessee
Although you can't purchase wine/spirits at stores in Cookeville, you can find liquor stores 7-8 miles away. There also is a new winery that opened a few miles outside Cookeville where you can purchase (and take it home

as it is considered an agricultural product (even though technically a dry county). Also, you are correct that you can purchase wine/spirits in many restaurants.
You may want to search in the main "Tennessee" forum as you will find a ton of info. about Cookeville.