We were recently adopted by a tuxedo kitty. He was apparently part of a litter abandoned by some renters that moved and left them. He is staying as an outside cat for now, much to the displeasure of our indoor cats that would love to have outdoor privileges.
We used to let Stella go outside on the deck of our boat and check on her every ten minutes or so. She would lie across the covered dinghy that was up on davits on the stern. People walking by on the dock used to stop and admire her - which she loved (and expected!). She fell in only four times in the three years we had her on the boat. When we sold it and moved into a house, her outdoor activities were OVER. That's been 7 years now but last night she tried to sneak out when I was fetching the bird feeder and I barely caught her before she nearly got to the steps. Guess they never forget that freedom, do they?
Just be aware that the outside kitteh can pass on diseases and pests to the indoor ones if he gets let in. It really is better for all concerned if he is brought inside for good. They DO get used to it eventually. Outdoor cats have a lifespan of only 3-5 years compared to 10-20 for indoor onlies.