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If it were me, I'd definitely not use a cattery. I never do that anyway, when I go away from home, I use a catsitter, and so my cats can stay in the comfort of a familiar and less stressful environment, where they are not subject to fleas and parasites and illnesses etc.
Whether you take Oscar back with you when you are visiting your family and friends, to me, would be dependent on the accommodations on that end. If you are pretty much always going to be out and about, visiting people and doing your own thing, and he has to endure a stressful situation at you mom's, then I think leaving him with a catsitter back in Aberdeen would be the best thing. Look at it this way: either way he's not with you, may as well be in a friendly environment when he's not. If however it's a pretty good setup, where he gets along with your parents, and they like him and interact with him, and peace can be made with the other cat, then that might be the most attractive option. I would pretty much base the entire decision on your estimation of how pleasant or unpleasant an experience he would have at your mom's.
To me, the car ride is not really much of an issue. Even if he is initially stressed out by it, I think with repetition that will be overcome, and it would be just a couple chilled out hours with you. Give him treats and such and make sure it's as good an experience as it can be. You can bring food and water for him. Give him a nice big carrier. The litterbox can usually wait.
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The little monsters 3
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