Obviously this is just another major chain restaurant that most people like to be snobby about and hate. But for a big work group going out for lunch it's a great choice. The menu, like most chains (I'm looking at you, Jack Astor's) has something for everyone. All dishes are expectedly mediocre. The prices are slightly above fair, but not completely out of line. Beer prices are $7-$8 before tax/tip so they can add up on you.
Last time I got a special - the lomo beef burrito. First, it's not a burrito in any sense of the word. Much closer to a fajita with pre-sauteed meat. The beef was actually pretty good if you don't mind your food being a little sweet. The waitress offered siracha to counter the sweet and it worked pretty well. I appreciate that they didn't skimp on the cheese like most places!
You know what you're getting when you go to Milestone's. I wouldn't go there for a date, but it's solid for a large business lunch with diverse tastes and low expectations.