what's best for my stray?
So I've been feeding Casper (my previous neighbors named him that because he showed up on Halloween) since the day after I moved in. I opened the door and he was on my stoop. He's been an outdoor only cat for at least 3 years. But he was also obviously an indoor-outdoor cat before that, because he's got to be the most affectionate and easygoing cat ever. He sees anyone and rolls right over for a tummy rub. He always wants to play with every cat and dog he sees, though he's pretty submissive around other cats. My current neighbor has a pit bull, and as soon as he sees her, even if he's in the midst of eating, he runs down from my deck to play. He also loves to tag along when the dog's being walked. He did the same with my previous neighbors
He loves it outside but a few times a year -when it's really cold, really hot, or raining - he stands by the back door and wants to come in. I feel so guilty and awful about not letting him in, but Celia's so easily stressed, and she's still skittish around him. He and Margaux coexist mostly peacefully on the deck, but she'd be really unhappy if he were in her space inside. My girls are both about 12, and I'm not going to upset them.
Lately, he seems to want to come inside more. He jumps up on the railing and tries to see inside, and I think he really craves more human attention than I can give him. So now I'm wondering if it wouldn't be better for him if I brought him to a no-kill to try to find him a family.
I bought a little doghouse and put it on my deck (2nd floor and covered). There's an outdoor heating pad inside, with a kitty bed on top of it, and I think it keeps him warm enough in the winter (I'm in Va; it doesn't get ridiculously cold), but still, it can't be very much fun to be stuck in his little house when it's cold or raining. He does just look miserable sometimes.
I'd love to have some input on which is the lesser of the two evils. Is it better for him to continue as an outdoor-only cat like this or should I give him a chance to be adopted? The mere thought of bringing him to a shelter makes me want to cry... But I'll do it if it's a better choice.