How smart are the gadgets that look at content for SEO?

Pardon my ignorance of terminology, etc. Question 1: If I have a blog about the best hot dogs in Chicago, but the website is named "Best hot dogs OF Chicago", will the preposition difference of in/of make a difference? If so how much? Question 2: If the website is instead about all the best food in Chicago, can I write "The best, hot dogs, pizza, and calzones, in Chicago" and the SEO robots will extract each phrase (i.e. the best hot dogs in Chicago / the best pizza in Chicago / the best calzones in Chicago), or will it get picked up only/mostly for people searching for all three at once? Thanks for enlightening me!