Many years ago when we lived in the city we adopted an old tomcat that was found on the streets downtown. He was incredibly affectionate. He loved me carrying him around like a baby, but man - he was tough! I've never seen a cat with skin so thick. More than one needle was bent trying to vaccinate that cat over the years.
He hated HATED to be indoors. That cat would YOWL and claw the door if you had him inside more than half an hour. All the tenants in our building (including us) went away one holiday weekend so we decided to set him up in our bathroom to keep him safe or we thought. We came home to him on the front porch of the apartment building giving us the Where were you? look. He squeezed through the 2-3 inches we had cracked the bathroom window, shredded the screen and jumped the
2 stories straight down to the parking lot. When I say the cat would risk dying before he would stay inside I am not exaggerating.
When it got really cold his first winter with us we tried to bring him in at night. We soundproofed the hall and bathroom (the most isolated areas of our apartment) as best we could, but he howled for HOURS even with us holding him - until we let him back out.
So we decided to call the local shelter to ask if they could give us any suggestions beyond what we had already thought of - on keeping him comfortable and warm outside. After explaining the entire situation in detail the girl who answered told us quite snottily that if we loved our cat we would keep him inside. So much for helping people.
We set him up with an insulated feral cat house that, of course, he refused to use. He stayed outside that winter, just as he had for all of his previous winters. It was safer than having him jump out another window or being forced to turn him in to the shelter for causing a disturbance.
We moved to the country a few months later. He lived out the rest of his life a very happy outdoor cat.
Our current boys are exclusively outdoors because that is what makes them happiest and we live in an area where this isnt a problem, but our previous three were indoor/outdoor. If someone lives on a busy street or has neighbors who dont appreciate visits from other peoples pets they might not have a choice, despite what makes the animal happy. We feel lucky that we can provide our pets with an option.