The Rails-to-Trails Library provides many useful resources about how to build rail-trails. The Art of the Rural Trail Deal seems relevant to many Kentucky trails. The common theme in it and really all rail-trail work is to build lasting relationships and cooperate with other people and groups in the community.
By many accounts, the best book on creating rail-trails is Secrets of Successful Rail-Trails: An Acquisition and Organizing Manual for Converting Rails into Trails. The book is available online in various formats and can be purchased from the Rails-to-Trails Conservancy. The Guide to Creating a Greenway or Trail also contains practical and helpful information.