I think it comes down to testing and looking at your data to see which way is working better for you. You'll find that keyword city will work better then city keyword and vice versa. As your friends how they search. Get an idea and test it out. Personally, I search keyword city.
Regarding finding the right expert, where they rank certainly does not mean that they are the best or most reputable. I'm sure it does indicate they know what they are doing when it comes to SEO but that doesn't mean they are a snake oil salesperson. A lot of local seo can be done by you, if you have the time.
A great place to start is by doing a Google search for Mike Blumenthal and David Mihm. They are very knowledgeable and very reputable in the local world. Figure out of you can do it on your own first then start seeking a firm/person to hire if doing it yourself is not an option. Word of mouth is typically the most trusted way to find someone reputable IMO.
"Give a man a fish and you feed him for a day. Teach a man to fish and you feed him for a lifetime." Chinese Proverb