I've built and operated in three states at one time: Texas. Louisiana and California. It's just replicating the same process. You get the state laws, a license for that state, the city laws, and start finding locations. You can definitely build and operate billboards in more than one state at one time. However, you have to be very good at managing your time. I used to set all my appointments in Los Angeles, for example, in the same week -- both landowner and advertiser. I then went there for a week and had nothing but meetings for seven straight days. Fortunately, much of what you need to do as a billboard owner can be done from anywhere (call advertisers, talk to landowners on the phone, file permits, send direct mail on ads, get bids to build signs, etc.). The bad news is that you have to physically be there to close most deals (new sites to build, signing up advertisers, etc.). So you just have to be a great multi-tasker, and have the freedom to go there when necessary. You might be able to run a different state just on weekends, to not take away from your day job, but with travel time, it would mean only maybe one day of meetings, tops.