Help me about website pages.
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Hi,
please read my previous answer to a very similar question at http://moz.com/community/q/is-this-good-or-bad-strategy
Unique landing pages for different locales are fine if you have unique content for each one of hem. That means one-of-a-kind reviews, images of the locale (landmarks), case studies, a map of a real business location for each location etc..
It is reasonable to presume that in your case that is easier to do for counties rather than cities. So go with the first option.
As for the third question: I understand your desire to optimise everything. But now I have a tough time thinking through the benefits that creating very similar service pages for each location might have for your users or for Google. Rather, it is reasonable to expect that those pages might be seen as very close duplicates of each other. For does your service really differ that much county by county? Probably, no.
A wiser choice is to do the following:
- Local landing pages for each county with a short summary and links to your service pages
- A separate services page(s) with some geographic customisation and links to the county pages to highlight where you operate
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Nice to see a fellow Wisconsin person here! I live in Bristol

Robert has some good points. Do you have any customer reviews that you can add to service pages? If you can add the reviews to the page with the date, city and state it should help.
On your contact us page, you can add a map with pins to the cities that you serve, with a link in them back to the service page for that county. That will help also.
The most important thing is having really great, descriptive content. I would utilize a blog to better geo target. The blog is so helpful because you target long tail key terms, make the entire content location specific and have really engaging, shareable information.