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THanks for your response. My only hestation with going to the vets is that it will add a bunch more trauma. He had a rabies shot and distemper 15 months ago and so probably still good (both the 1 and 3 year shot usually last 3 years) and so it would only be to knock him out and check him over. Not sure if that is too much . .. .I don't know.I have been following your story and just wanted to add my thoughts. As there seems to be no one who could take care of Oscar when you leave and he is so used to you feeding him, it wouldn't be in his best interest to leave him behind. You are doing the right thing by keeping him with you. You can always think of this move as a first step. Who knows what might happen! There might be a day in the future where you could take him for walks on a harness. You might expand the catio. You might add cat-proof fencing. Or you might find he is perfectly happy in the new home that you are now providing for him.
I have taken in two outside cats (one semi-feral, one stray) after feeding/sheltering them through several winters. I kept them in a separate bedroom for months where they were perfectly happy with a window, food, water, litter, a cat tree, and a soft place to sleep. The semi-feral cat wasn't really interested in leaving the room when she had the option!
As far as the immediate decisions, I think it would be easier for both of you to take him directly to the vets. That way you won't have to trap him again and he can be checked, receive shots, flea medicine, etc., then go to his new home. When he is in the trap, as you probably know, it is important to cover it up and most cats immediately calm down. I had to keep one of my cats in a trap overnight and he was quiet as a mouse!
Best of luck to you and thank you so much for caring for Oscar!