wizball The deactivation on WS 2008 R2 can occur when you install the ESU key and then install the January 14, 2020 security only update (KB 4534314) or January 14, 2020 monthly rollup (KB 4534310) on the ESU activated Windows Server 2008 R2 computer. It might cause ESU to deactivate and need to be reactivated. It is mentioned in KB4538483 . It does not impact Windows 7 nor Windows Server 2008 SP2. The ESU Licensing Prep Package is not involved.
On Windows Server 2008 R2 you can avoid the reactivation issue if you can install either of these January 14, 2020 updates before ESU key activation. To simplify things at this point you might install the ESU Licensing Prep Package first (KB 4538484 for WS 2008 SP2 and KB 4538483 for WS 2008 R2/Win 7) and then activate the MAK key. This saves you from having to verify which monthly rollup needed to be installed prior to the availability of the ESU Licensing Prep Package.
Gdoc74 Unfortunately KMS is not an option. Take a look at this post and see if that may work as an alternative.