I've been living in Cookeville for two years. It's an alright city for the most part, but there are a couple of areas it can improve in. Cookeville itself is fairly busy and there's usually enough fun things to do in the city. On the other hand, the crime rate has gone up a bit over the last few years.
Most of the local jobs aren't too high paying, so you may need an extra side job to compensate. Plus, you're almost two hours away from Nashville so commuting for work is out of the question. On the other hand, Cookeville has a couple main shopping districts where a lot of the stores are, and they're close together so it doesn't take long to drive between them. Jackson Plaza, the main shopping center, is probably the best area in Cookeville.
The summers are very enjoyable, and there are a lot of activities and performers in the area, so you'll probably be able to hear a lot of local country singers.