Like many women she loooooooooves attention. Chills right the fuck out when I let her sleep next to me on my bed without orangie bothering her.
Ferals are like that, very suspicious. Try rubbing your hands against the food bowl and around the area he's eating. He'll become mire familiar with your scent and eventually you can start getting closer. Also if your worried about winter buy those warm closed top dog beds and attach it to a climable perch and he'll probably ignore it but atleast you tried. If you take him to a shelter he'll be put down in 2 days. Shelters don't adopt ferals, they just put em down... =(