It is a chicken and egg question for sure. Clubs/festivals want to book good performers - which requires lots of performances to become good. There are always venues that will let people play for free (I wish they would pay even a small amount $20, for example, just to offset karaoke). The bottom line, though, most places are only interested in one thing - how many people can you bring in who will spend $$.   

Two good recources for making a plan for yourself - yes, it works much better with a plan:

www.cdbaby.net - click the "Advice" tab.

www.soloperformer.com