Steve has a new advertising budget to expand clientele, focusing on 30-50 year olds in Southern California. The budget includes SEO, pay per click and other advertising. Leo says that SEO or search engine optimization, is largely snake oil. It can help him, but it doesn't make a huge difference. Leo would advise separating that out of his advertising budget. As for advertising on Bing, he should check the market share. That may not be a good place to put it.
For Leo's money, he would look at the last presidential campaign, where the candidates used Facebook advertising both efficiently and effectively. He can target his audience with laser focus. Facebook knows a lot when it comes to demographics. He can also give Facebook a mailing list and they can match it with members that have similar demographics. That's why Facebook is getting the lion's share of advertising.
Google has great information on AdSense and ad words. Marketing Land is also a good resource. But it's important to know that advertising online is just as much art as science. If done right, $5,000 can go a long way and easily pay for itself.