LFJV: Build a Community Website (offline ?)

I'm situated in a small town of about 8k but there is tons of tourist traffic driving through and seasonal work that brings the hotels to "No Vacancy" for months at a time. I want to build a free business directory via Wordpress MultiSite / Buddy Press / Directory Press. WP MultiSite to give free webpages to charity organizations and local "personalities". Monetize via groupon type offerings, coupons, featured listing, making contacts with businesses for offline services, etc. My current location has 60k desktop and 18k mobile searches for the town's name. In about 6 months I'm moving to another location where I will have access to 4-6 cities of several hundred thousand within an hour drive.

I would like to make this a case study. And apply the knowledge in my future location. I imagine the thing would be to get the "directory" ranked for for everything i.e. someone types in "townsname pizza" and our directory should come up first.

You already have something like this set up or you have experience you can bring to the table. I'd like to stick with WP / MultiSite instead of something like CouponPaq.

Please let me know if you can assist in this venture or can recommend another person.