From a purely legal, follow the license agreement perspective:
OEM licenses are non-transferable. An OEM license only permits you to run Windows on the original system that the OEM license was distributed with/first installed the license on. The upgrade can only be installed on this original system.
Retail licenses are transferable. As such, you can retire a computer, move the retail license to a new system, and then install the upgrade on that system.
None of this addresses the technical ability of what you are able to do...
Intel i7 4790k @ stock, Asus Z97-PRO(Wi-Fi ac), 2x8GB Crucial DDR3 1600MHz, EVGA GTX 760
Samsung 950 Pro 512GB + 2TB Western Digital Black
Dell 2408WFP and Dell 2407WFP-HC for dual-24" goodness
Windows 10 64-bit