PIF-Peanut Butter, Stubby, Lucky and Maggie Sue were much older ferals when we got them in so they spent many months outside. They never got over that and will swing from the curtains if they are not let out. It has taken me years to finally wean them down to weekend mornings.
We have a small neighborhood park right behind our house which was recently refurbished. Lots of big new play stuff for all the kiddo's but because of that traffic has also increased. My fear for these guys is great but I give in to them early weekend mornings because there is virtually no traffic during those hours.
We got Sammy when we lived in an apartment so he never went out. Leroy used to go out until he disappeared for three days and came home terrified. He didn't want to go out again for awhile so I took advantage of that and just stopped him all together.
The last three were pretty young when we brought them in so they are used to not going out and don't even try.

My dream someday is to screen in our large covered front porch so all the kitties can feel like they go outside.