The hardware version on a VM dictates the maximum version of VMware Tools that is pushed by vCenter.
When pushing upgrades of VMware Tools, one should also consider the version of the DVSwitch, as some OS's may have problems if you have upgraded the VMTools and not the switch, or the Hardware compatibility and not the switch.
A good order to do the upgrades in:
If the VMware Tools upgrade fails from an automatic deployment from VMware (Lifecycle Manager, Manual push from VCenter, etc.) then an attempt to rollback will occur, and the upgrade will be marked as a failure so that it doesn't re-attempt until the VM can be examined. Sometimes the rollback can fail as well due to issues inside the VM. Recommend having a snapshot of the VM before doing the upgrade.