If my understanding is that you want to build a website like "yelp/local business"...then I think you need to go out and talk to local businesses about how their needs aren't being met by craigslist, yelp, etc.

Also from the description, it looks like you might be going after too many things. For instance - if I am a small town plumber, chances are that I am not going to have a commercial to upload. This will make me look less professional on your website and I won't like it so I won't use you. On the otherhand if you had statistics like the number of "jobs" that I have done in the last month at or under the price quoted, then this would be helpful for me as a customer.

Perhaps the way to go is to make a website that lets very small local business construct advertisements that don't suck. Make it painfully easy for them to do this and they will pay money.