We only use computer based software installation policies, but would like to convert to user assignment for laptop users who mostly use their laptops out of the office.
They have admin rights, so software installation won't be restricted by lack of installation rights.
Since they are going to using these laptops outside of the office, even with VPN, they cannot get computer assigned software installed because the VPN connection cannot be started until the computer boots to the login prompt. Assigning software to the user should allow the software to install over the VPN connection if they start the VPN connection prior to logging in to Windows. Mandatory software can be assigned and optional software can be published.
Not assigning software to the workstation should allow us to re-enable fast login optimization so the users don't have to deal with painfully slow boot times when out of the office while their laptops attempt and then fails to connect to the non-existent domain network during every startup.
The only issue I see is that we need to make sure the software only installs once and does not install on other computers they may log into that are not assigned to them.
I assume this can be accomplished by assigning the GPO to the workstation and then using group policy loopback processing to assign it the user when they are on that specific computer only.
Is anything else needed? Are there other problems with assigning software to users vs computers?