Hello PTHerrington,
You certainly have your work cut out for you, that's for sure.
If I were you, here's what I'd do:
- Analyze where my competitors are weak when it comes to online local marketing, and exploit those areas especially. It sounds like the main advantage they have are offices in those towns, which you can't duplicate. I personally wouldn't bother with the PO Box option. I doubt it will help a whole lot with your end game from actually netting more customers.
- I'd start with a good Google AdWords budget while you're trying to build rank organically. Over time hopefully you'll have to spend less and less on AdWords, but out of the gate you'll need it to get traction over organic competitors. Ideally you'd have really good landing pages that drive them to a page for that town, or county if towns are not feasible. (Of course, if you worked hard on a handful of pages for individual towns for organic, those could double for PPC nicely.)
- People generally don't search as much for services on a county level. So I'd argue you should focus on a few small, key town pages, and try to fill them with as much local content as possible and try to educate your consumer a bit, beyond what your competitors are doing. Over time those pages could get rankings, but doing the H1 county thing with H2 town names I don't think will deliver.
Here's an example of a woman who created good local content and from it grew not only a pet sitting business for herself, but a thriving franchise business other pet sitters have replicated in their cities. I'd assume her area was dominated by larger kennels etc., and she appears to be a one-person operation. http://www.copyblogger.com/bella-vasta-case-study/
- Be sure obviously to check out Moz Local, and listen to Greg Gifford's webinar on local SEO. He helps local car dealerships, and that webinar is packed with good, practical ideas you can execute on.
In summary, I'd argue don't try to cover everything. Just pick a few towns and test out what works, and then slowly expand out with additional pages. You can always mention other cities you operate in. But don't try and bit off your entire coverage area with regional pages.
Most companies do little more in local SEO than register a Google Places page and have a physical address. So if you try to create a little more value and optimize heavily for those towns, over time I bet you'd see some good results.