"Barn cats"
My parents had 'barn cats' when I was young, and they did just fine. As long as they are 'fixed' and have their vaccinations, we didn't see the problem with it. It didn't impact their lifespan; I think one lived to 17+ years! Seldom do I recall them ever having run-ins with other wildlife (or other cats, for that matter). And, fortunately, never a skunk incident!
We spent time with them when outdoors, and they were happy and healthy kitties!
I've also had indoor cats; pros and cons can be said for both! Not having a litterbox to clean has its merits! (Just remember to cover the kids' sandbox outside to prevent that problem with any outdoor kitties!)
The tricky part about your situation is that you'd prefer the younger kitty to be 'indoors'. I'm not sure if that will last; sounds like s/he can scheme ways to 'escape' with other pets around! Maybe it's better to let them explore once they're old enough to go out without getting hurt or lost?
Anyway, That's my 2 cents...
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