This was on my mind all last semester, but I just do not have enough speaking experience with Latin. I just picked up Conversational Latin For Oral Proficiency by John C. Traupman with the hope of teaching myself.
I just got back from the Society for Classical Learning conference where there were some good breakout sessions on oral Latin. You might try to get access to these seminar recordings–I think they might be of help and encouragement.
Here are three leaders of oral Latin I have met:
Will Kilmer (Veritas School, Richmond, VA)
Tim Griffith (New St. Andrews College, ID)
Marcus Foster (Covenant Classical School, Ft. Worth, TX)