TOPIC: How did you pick your 5 cities?

I'm really struggling with picking 5 cities.  There could easily be 50 cities I would go to within 20 miles of my home town.

If I think like a consumer, they would pick the large town nearby them and search that city.  So should I just pick the 5 largest cities within my "preferred" driving range?

At this point, I'd probably drive much farther than if I were busy.

That's exactly what you do. You choose the 5 largest cities near you. Preferably over 40k people. You still create the city specific pages for other cities, but the top 5 are what you focus on all over your site.