"Stupid simple" is only half right.
To me that's a lot of hassle to get basic functionality from a $500 dumb terminal. Better to spend $350 on a laptop, then use printer sharing on that desktop machine. Printer sharing is something that is in all major os's since Windows XP at least. This solutions allows you to print from any app on your laptop.
Better still to perhaps print from the desktop machine which is wasting space, money, and electricity acting as your print spool.
[1] of course cloud ready printers will become more available, but they are rare in the market atm
He's either got to buy a compatible printer (extra cost) or set up a windows machine too. It probably has to be on. Not the end of the world (and might be just right considering the family computer situation), but I stand by the notion that there are more potential points of failure.
I hate printers, printers in Linux have actually been easier than printers in Windows for me lately if you're willing to walk to the printer and determine the IP Address or hostname.
But Cloud Print makes it stupid simple. Install it on your desktop connected to the printer via basic USB, then login to your Google Account. You can now print to that printer anywhere in world from Chrome. Seems pretty easy to me.