Another guest at the farm

Lynn and I have been trying to get close to this little guy for weeks now with no luck. He has a highly developed fear instinct and bolts usually at the sight of us. We started leaving food outside for him and slowly moving that food into the barn, in an effort to get comfortable in there. My hope is that he sleeps in there to escape the elements. It appears as though he does.
So we leave food in the barn every morning and every night as well as leave the barn doors slightly open so he can find shelter. Not sure how we are going to handle winter with him. Leaving the barn doors open is not the best idea. I think we should put in a cat door, Lynn does not agree. What to do! Should I just pull a Nora and buy and have Jim install the cat door? Probably. Even though this little one is a major snot-head for not liking us, I feel responsible for his well-being. And obviously Lynn does cause she is the one who started feeding him in the first place. Damn we are suckers. Little stinker dude.