This is an interesting situation:
1. $1,000 will get you a lot of capable dual-core laptops that will do the job nicely - but they're not really 'gaming laptops'. These are typically quad-cores and above $1,000. But Christmas is coming up, so you never know...
2. As for upgrading laptops: You can only upgrade RAM and storage, and more and more laptops are sold as sealed-off units meaning you're not supposed to upgrade them even if it's technically possible - if you try you'll void the warranty. This means you should always spend your money on the components you can't upgrade, i.e. the CPU and the GPU. Then, depending on the laptop, you can save up for more RAM or a better hard disk down the road.
From newegg.com here's Candidate No 1:
https
/www.newegg.com/Product/Product.aspx?Item=9SIADYY6GM9425
This $980 Dell actually packs a quad-core Kaby Lake i7 and a 4GB 1050 card. RAM can be expanded from 8GBs to as much as 32GBs, should the need arise. Right now, the 4GB 1050 card is massive overkill for the games listed, but the moment your son decides to 'upgrade' his gaming preferences, this card will handle most of the sophisticated AAA games he'll come across. The only weak point the is TN panel, but going by your son's schedule I don't think it's going to be that much of an issue.
NOTE: This Dell is sold by Dell through newegg.com, and I advise you to read some of the user reviews for this seller - it seems to be a mixed bag, but some of the negative reviews can be ascribed to increased holiday traffic. But see for yourself.
If you're not totally sure about the newegg listing, there's this (almost identical) alternative from BestBuy:
Candidate No 2:
https/www.bestbuy.com/site/hp-omen-by-hp-15-6-laptop-intel-core-i7-8gb-memory-nvidia-geforce-gtx-1050-ti-1tb-hdd-128gb-solid-state-drive-hp-sandblasted-hairline-brushing-and-carbon-fiber/6123334.p?skuId=6123334
From HP this $900 Omen is very similar to the Dell above - if rather more 'in your face'. RAM can be upgraded and storage expanded as needed, and most of my comments about the Dell apply to this Omen as well.
This laptop is sold by BestBuy (not a third-party vendor) and you can click the blue Reviews button to read user feedback.
Best of luck to both of you,
GreyCatz.
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