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It's going to be hard to give an exact answer as the sites have now changed.  But, if your rankings dropped a month ago I'd be looking at Panda as a culprit.  There was a Panda update that officially happened May 20 but many people saw changes a few days before that.

"How does google decide if a listing from one city shows up in another?" -- It depends on the amount of competition that search term has and how well everyones Google Places pages are optimized for that term.  If there is a lot of competition for that term then it will stick with that city, if there are not a lot of quality matches it will expand it's results. "Any ideas on improving the distance your listings show up for?" -- Optimize you Google Places page for the keywords you want to show up for. Your Places page is going to be centered around your physical address first, then it is going to look at the content you added for title, description, and any other info you add.  If your business covers a wider area like a neighboring town then make sure you include the name of that town in your description or title if it is appropriate. Your success will depend on how competitive the market in that area is and how optimized your page and others pages are for those location you are looking in.

Yes each link text will help you rank for thet lihnk text. but if your page is not optimized for that term it mayy be a waste of effort. I often send links to my clients sites buy using the brand names of his coompeditors in link text. this brings him  up underneath them on search engines which is better then nothing, but he will never beat them as his page is not optimized for the term.

Google will do what Google will do. Just as results change when the query deserves freshness (think how search results for osama bin laden changed dramatically within two hours) so do some results deserve local emphasis, in google's mind at least. If the places results show up after the top three, then getting into those top three is the same as any other top three. If the places results are showing up before any others, there's nothing you can do to get yours ahead of the places results, that's just where google puts it. some searches even spread the places results out. A search for payday loans brings up A from the map as #1, then no places results again until #4. The key is SEO is SEO, so always have good, unique content and get good links and you will move up as high as you can.

Do you recall what the cost was? I'm considering it for a few of our clients.

It could be the case of different browsers hitting different data centres which have not yet consolidated their rankings.

I believe that there's a general misconception of what content is. Infact, people tend to think at is a "written content". But it not so. Video and audio (both better with transcripts), photos, graphics (and infographics), and, yes, written posts are all contents. As Adams said, the secret of succes of any enterprise blog happens when it is able to become a relevant and authoritative voice in its market.

Oh - and one last suggestion - just above the two addresses in the bottom area of all pages, have a statement about how you serve Brevard and Collier counties.  So something like "The Musil Law Firm has been serving Brevard and Collier counties since XXXX".  And have a similar but unique statement to that on your home, About and Contact pages directly in the main content area of each.