As the solution for "Workin' nine to five" points out, it's not very efficient to try to do this at the same time as you get the Team Dash achievements. Let the Team Dash matches end in draws so all four players get their wins, then split up into groups of two and go for this achievement.
This achievement alone ended up taking us around 90 minutes despite that.
Using the latter restaurants (we liked the third one, Flo's seafood whatever it's called), each match can be done fairly quickly. Just try to chain everything and buy new tables for all your money.