In regards to the OEM-like upgrade, I'm not sure what you mean. Most store-bought PC's come with the key sticker (not sure about 7/8, but in their case you can get it from the System screen.) My bet would be that if you have the key for your original OS and the key for your free copy of Windows 10 upgrade that you would be able to install and upgrade (though, it wouldn't surprise me for it to be as you stated.) I've personally never run into a situation where I couldn't transfer a copy of Windows to a different PC (I have several keys from laptops/desktops that customers have donated to me after I've built them a new computer and they bought a newer OS and I've been able to install those on other computers/VMs.)
I'm excited for it. I love 8 and from what I've seen they've taken the best parts of 7 and the best parts of 8 and put them together.
OEM licenses will not let you transfer the license to a different machine. Retail licenses let you move your copy from one machine to another. This is generally enforced when you try to register your copy, as an OEM key will already be flagged as in use with a particular hardware setup and therefore the server will deny your authorization request if the hardware differs.
(I do not know if Win10 will use such a license for the upgrade, just stating it as one way they might justify the free cost)
I've never had an issue with OEM installs as long as I used the same installation files the key was tied to.