The only key to marketing on Craigslist is making sure that you don't duplicate your content. You don't even want to have similar content on your ads because Craigslist will still get you for it. If you are going to create different ads in different cities, they have to look as if you were two or more different people. I'm not saying that they aren't going to know the source of any of the ads, but I'm telling you to never give them a reason to flag you or ban you altogether.
All you really need to do is make sure that you mix up your ads a little bit. You can add pictures to some of them and not add any images. You might want to mask your links under different cloaks as well. This will help you not look spammy or look like you are trying to monopolize Craigslist....lol.
The bottom line is you have to mix up your efforts so you don't draw any attention to yourself.