Re: Can a cat be comfortable in two homes/territories?
Welcome to CatForum!
I think, as long as his "family unit" is still together, and he is made (at the ranch) to stay inside for at least a week, so he *knows* where his food/people are and can become accustomed to his new home...then try going outside supervised (with you or wife accompanying him) as he is allowed to become familiar with the new area for a few days... I think he should do fine. The goal is to make him feel comfortable in the new home and then help him get familiar with the exterior area of the new home, so he knows where to come to get back inside and how to get home from his explorations.
If any problems arise, I think they would come in the form of being nervous at first, just because it is strange/different, but like I said, if his familiar people are with him it won't be awful. IME, indoor/outdoor cats are very adaptable and tend to be pretty laid-back with few behavioral problems. Overall, I think probably the biggest challenge, will be him having to carve out his territory every 6mo. There is a good chance that he will have to establish himself in the new (ranch) area AND when he returns to his other home, other cats may have moved in and 'staked a claim' to that territory while he was away.
Keep up-to-date on his vaccinations and watch for any catfight injuries that could abcess. I would also de-worm him through the vet (droncit for tapeworms) because he will get worms from any prey he may eat. I'd also deep him steady on Revolution to help control fleas. I'm not sure, but I think Revolution also kills some worms?
Anyhow, just use common sense with him until you see he is relaxed and familiar with the new home and the new territory around the home, then I'll bet he's gonna have some fun!