Living in Nashville for the past 30 years, I've had the pleasure of seeing Jim and other great artists many times. Jim, Marty Stuart, Buddy Miller, Emmylou and several others often host charity events, music celebrations, and local shows that are free or low cost.
The Americana Music Festival is something you may to attend. Also there's a cruise called Camayo that is like a week long music festival on the water. Buddy Miller often hosts and plays with other artists.
Music City, USA