In VUM 5.0 We have option to automate VMware Tools update during the Power Cycle so when you have a schedule downtime
What's New
VMware Tools Upgrade: VMware vSphere Update Manager 5.0 enables reductions in virtual machine downtime when upgrading VMware Tools by reducing the number of reboots required. You can schedule an upgrade to occur at the time of next virtual machine reboot.
http://pubs.vmware.com/vsphere-50/topic/com.vmware.ICbase/PDF/vsphere-update-manager-50-install-admi... (Page 132)
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