What does he play? For an all around gaming system able to handle heavy duty games like Fallout 4, Witcher 3, Star Wars Battlefront, Battlefield 4, etc at 1080p I'd go with an i3-6100 and a GTX 960 4GB. If you're able to snag a Windows license from work, this would be a nice build with lots of room to upgrade:
PCPartPicker part list / Price breakdown by merchant
CPU: Intel Core i3-6100 3.7GHz Dual-Core Processor ($125.98 @ Newegg)
Motherboard: ASRock Z170M Pro4S Micro ATX LGA1151 Motherboard ($102.98 @ Newegg)
Memory: Mushkin Redline 8GB (2 x 4GB) DDR4-2666 Memory ($57.99 @ Newegg)
Storage: Western Digital Caviar Blue 1TB 3.5" 7200RPM Internal Hard Drive ($51.99 @ Newegg)
Video Card: MSI GeForce GTX 960 4GB Video Card ($211.98 @ Newegg)
Case: NZXT S340 (Black/Blue) ATX Mid Tower Case ($64.99 @ Newegg)
Power Supply: XFX TS 550W 80+ Bronze Certified ATX Power Supply ($51.99 @ Newegg)
Total: $667.90
Prices include shipping, taxes, and discounts when available
Generated by PCPartPicker 2015-11-20 12:41 EST-0500
That also comes with $45 in mail in rebates that I didn't include. But if you do include MIR, you could go up to an i5-6500 and after that $45 in rebates you'd be at $701.91.
PCPartPicker part list / Price breakdown by merchant
CPU: Intel Core i5-6500 3.2GHz Quad-Core Processor ($204.99 @ Newegg)
Motherboard: ASRock Z170M Pro4S Micro ATX LGA1151 Motherboard ($102.98 @ Newegg)
Memory: Mushkin Redline 8GB (2 x 4GB) DDR4-2666 Memory ($57.99 @ Newegg)
Storage: Western Digital Caviar Blue 1TB 3.5" 7200RPM Internal Hard Drive ($51.99 @ Newegg)
Video Card: MSI GeForce GTX 960 4GB Video Card ($211.98 @ Newegg)
Case: NZXT S340 (Black/Blue) ATX Mid Tower Case ($64.99 @ Newegg)
Power Supply: XFX TS 550W 80+ Bronze Certified ATX Power Supply ($51.99 @ Newegg)
Total: $746.91
Prices include shipping, taxes, and discounts when available
Generated by PCPartPicker 2015-11-20 12:46 EST-0500
I added the Z170 board and the overclocked RAM to give the option to add an unlocked cpu later on and because when cpu bound (which is going to happen in modern games with an i3) the RAM speed can make a real difference. See the review of the i3-6100 on Digital Foundry's youtube page to see what I mean. Also, going with an H series board you'll be stuck at DDR4-2133, but getting full speed out of your RAM on a Z series board is as simple as just selecting the XMP profile from the BIOS. I also put a power supply that is pretty overkill for an i3 + 960, but it's a high quality unit (Seasonic OEM) in case your son wants to add a higher power GPU and/or CPU later on, since you want upgradability.
The case is pretty nice, the NZXT S340. It's got great build quality, pc gamers love windows in their computers, and it's easy to do the cable work for a clean build. I was thinking of buying this case myself after checking it out firsthand at Altex, though I opted with a Phanteks Enthoo Pro instead because I love full towers. The S340's window does scratch really easily though, so make sure your son knows this if you end up getting it. Also, note the one I picked in those builds above has different colors from the one in this review, as the all black one was more expensive.
Since you want an upgrade path Skylake is the only way to go. Intel isn't making any more chips on LGA 1150 while they'll be making Skylake, Kaby Lake, and Cannonlake on LGA 1151, so the earliest you'd see a new mainstream socket is late 2017, though I'd bet more on late 2018 since I doubt Intel would just want to punt Cannonlake like they just had to do with Broadwell.

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