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I'd rather have him choosing his own roommates and managing that aspect. That is exactly the situation he is in now where he is one of the roommates paying rent to the guy who's name is on the lease. That seems to be fairly common down there.
...I wasn't necessarily after simplicity.

That's not a problem. Let him do the choosing and then the roommates sign the lease (with you as the lessor.)
Other things I should be considering here?

Probably not too much, from a tax angle.
As to your son living there, being a family member, make SURE you're getting a fair market rental from him. Otherwise you're deemed to be using the property personally, and that drags you into the "vacation home rental" rules.

As to your son being on site and looking after the place on your behalf, and it's in a distant city, I question whether it qualifies as an "active rental" for the PAL rules.

I can't think of anything more that would make it complicated.

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