Ranger is also an old man (15 years old). He isn't as timid as Sammy. When we were living in Bolingbrook, IL Ranger decided that he wanted to spend time in the back yard, so he started sitting by the back door. I started taking him out, and found him to be very well behaved. He never tried to climb or jump the fence, but was content to just explore the yard and occasionally stalk any squirrels or bunnies that happened in to the yard. He would explore for a while, then come hop into my lap for some snuggle time.
When we moved to KC the weather was awful! Snow on the ground with more falling frequently, cold winds blowing, occasional sub-zero temperatures, etc. We were able to spend a few very short session checking out the yard, but neither he nor I could take the cold for too long. The last weekend in March, 2019 the weather finally broke. We were able to spend half an hour or so out back, and Ranger explored most of the perimeter of the yard. I intend to get some patio furniture out back soon, so we can spend our afternoons doing lap snuggles again.