You will definitely want to get him neutered. It helps with the whole roaming thing.
One of our cats is a bit of a flight risk, too. He's just curious. What we do is walk him on a leash/harness sometimes to give him the opportunity to get some supervised outside time. If you start Smokey early, he will probably learn to handle the harness and you can walk him like a dog.
I get the funniest looks from people in my complex when I walk Anchovy. But, he's happy so it doesn't matter
