re: Update: I am in Rebel Bear country for the first time.

It's a little more expensive, but if you can swing it, stay at the Fairview Inn in Jackson.

Places to eat in Jackson:

Parlor Market (expensive)
Walker's (expensive)
Babalu- one of my favs (reasonable)
Julep- get the fried chicken (reasonable)
Pizza shack (reasonable)
Sal and Mookies (reasonable)
Keifer's- good gyro (cheap)

Bars:
Fondren Pub
Fenians (Irish Pub)
The Bulldog