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Hi, this is Dr. Sara. You have certainly taken on a challenge. My thought is that maybe he was more of a farm cat vs a pet. He probably enjoys attention when he is outside but does not want to be in a house; he probably feels trapped. He is not used to it. I am not saying it is impossible, but he may develop some undesirable behavior issues like peeing in the house. Are you in an area where he could go outside?
I see. Are you in a city? and can't allow him to go outside a bit?
It's a good sign that he will cuddle with you. Maybe trying some special things to eat to make being inside not so bad.
If you are able to let him out then I would get the collar, keep him in for a little longer so he knows where home is and then try letting him out a little at a time. Maybe have some food on the porch/steps during the day to keep him close. Then trying to get him in at night. I think this may work but I don't see him being 100% indoor for the rest of his life. I think he'll show other behavioral issues.
Yes, that sounds like a good idea but I think maybe another 3-5 days so he knows where home is. The one thing you could do is give him a pet container to get into at night if he doesn't come in before you go to bed. My in-laws always had an Igloo Brand pet house that they put a wind block on the entrance and put straw and blankets in there. That way if their cat came home after they went to bed, he had a warm place to crawl into.
I totally understand. I have had indoor/outdoor cats in the past and I always worried. He is smart being outside, just keep reminding him of your affection and food! Good luck!