OK well conversation closed with scoitland so here goes. In Tasmania i had several cats, a number of whom ended their careers very rapidly on the roads. THey were all kept indoors at night but otherwise outdoor cats - I lived i the country then. I got sick of the road carnage and when I moved into my third house I had a stable with a loose box and yard which I enclosed with mesh so that the cats could be out during the day and inside at night. I also had breeding queens at that time who were indoors all the time. Some of the cats had been outdoor cats before this but adapted very well and in the evenings, they would follow me down the hill from the run, stopping off to say hello to my stud male, and come inside no problems.
In NSW I obtained Bobcat who was 5 years old and had always been an indoor cat. I kept him indoors for three more years until I moved to Brisbane where he started going outside, as he had, by then been joined by Pavarotti, a siamese of some notoriety. Bob's first venture outside was accidental, and I was not aware he had gone out. He woke me at midnight leaping up at the side of the house (these houses are on stilts) and slowly sliding down the side of the wall to land with a thump. After that he, and Pavarotti were let out regularly, still sleeping indoors. While at that house I also aquired Claudius, a half abyssinian. Claude used to get into lots of fights and spent all his time at the vets being patched up or being treated for abscesses. Bob, who by now was 11, injured his leg jumping over a fence and getting caught half way. That year I spent over $5000 in vet fees. I looked around and discovered a company that installed cat runs and had one fitted to the side of the house so they could come and go, but be enclosed. It worked well and they were all happy and adjusted no worries.
I then moved to another house in Brisbane which had three wildlife reserves, and an equal number of major roads around it. The garden had been landscaped with native plants so the place was crawling with wildlife. I installed an amazingly complex series of runs that had tunnels at ground level and aerial tunnels, as well as pens that enclosed whole trees. Access was via an aerial ramp from the bathroom window (about 18 feet up) to a tall cage around the trunk of a paper bark. They had a choice of a series of shelves or climbing down the tree trunk to get to ground level and several other 'rooms'. Once took then through the fence onto the grass where the dog was. So they could have grass (which I grew long as a jungle) bark, or stone surfaces as well as trees to climb and other bits and pieces to play with. Again, they adjusted incredible well, no problems.
Then along came Ralph, who belongs to a friend but who came to stay for a couple of months while she sorted out her life having just left her husband. Ralph was not happy. we moved to New Zealand and as the neighbourhood was a quiet one, they were again allowed out, but inside at night. Ralph hated this. He expressed his hatred by peeing on everything in sight. Walls, doors furniture, bedding, christmas trees, nothing was sacred. After two years of this, he was returned to his owner who allows him free range day and night. He is the perfect kitty... So, I guess it depends on the cat as to whether it will work or not.