Can I use my USB stick with install media to upgrade without issue?
Your Windows 10 Professional license is a digital entitlement. This means you can install Windows 10 Professional without entering a product key, and the installation will automatically activate, because you activated your original installation of Windows 10 Professional before the July 29th 2016 deadline.
Would I have to first install 8.1 Pro and then upgrade from 8.1?
You never had to do this even before the changes to 1511, which allowed you to enter your Windows 8, Windows 8.1, or Windows 7 product key to activate your Windows 10 installation on hardware where it had never been activated on. Since you activated Windows 10 Professional, before the free upgrade offer deadline, you can simply install the current version of Windows 10 (1607) and it will automatically activate.
I know I can clean install just fine, but I'd like to avoid having to
reinstall all my programs and such again. I can't seem to find a
You can acomplish this by doing the following. You will need to upgrade your installation to Windows 10 Home. You then upgrade Windows 10 Home to Windows 10 Professional, using the generic license key, VK7JG-NPHTM-C97JM-9MPGT-3V66T. Once you are upgrade to Windows 10 Professional, navigate to
Settings > Update & security > Activation > Change the product key and enter your Windows 8.1 Professional license key.
How to upgrade to Windows 10 pro from Windows 7 Home
Technically you will have to "lie" and use the "free upgrade" even after it has expired. The free upgrade offer is only being extended to users who are using assistance programs currently. You would have to indicate that this applies to you, since you have the intention of upgrading to Windows 10 Professional using a key that was already used to install Windows 10 Professional, I see no reason to at least attempt the upgrade. Of course once you upgrade the installation from Windows 10 Home to Windows 10 Professional, you will have reached the point where you cannot return to Windows 7 Home.
The user who asked the original question submitted the following response couple days later so I suggest you give this a try.
All done and working as advertised!