Potentially buying an established vending business. Questions to ask?

I’m meeting with the owner of an established vending business/route next week who is interested in selling. I’m new to this and business as a whole so I’m just looking for a little guidance. What questions should I ask and what information I should know before taking over a business like this? What would be a reasonable purchase price of this business? Like I said, I’m a noob so I’m just trying to walk this path wisely.

A couple things to note;

•20+ Machines (all w/ cc readers)

•12+ Locations (all within 20 mile radius)

•Gross Roughly $100k/year

Any help and insight would be greatly appreciated!