From what Ive seen most people do around 2500-5000 to start. Not sure on time span.

I am working on this business idea myself right now I will be sure to post my results. I have a lot of other stuff going on so not able to dedicate much time to this but so far I have made some business cards, websites, and picked up a couple of takeout menus + 11x17 legal paper to copy them to + advertisements.

Once I finish the website I figure I will go get approval from restaurants, and then I'll find advertisers. Last time I tried this (when I had practically no time at all to work on it so I never finished) I had a difficult time getting only one person to pay me $100 for an adspot, let alone $290 ...

I think I am going to offer like $50 per thousand ads or maybe even less. I'll have to see what people are willing to pay I will of course start higher.