What version of Landesk are you currently using? In our 2016 version we've included "inter-package actions" in which you can add a "reboot" action between your packages. This functionality is applicable to bundle packages only.
In 9.6 when utilizing a bundle, if your reboot settings are configured to "act as if a reboot is always needed" we will reboot after the package installation. The "detect whether a reboot is needed option" may not sense the need for a reboot if Windows doesn't list a reboot flag in the registry after the uninstall script is ran. This functionality in your current build, if in the 9.6 environment, is not working as designed. We had an issue with Bundle packages not continuing on after reboot, which has been addressed in our latest 9.6 SP2 component patch (CP) (0323) and you will have to request this CP from support by opening a case.
In the interim, you can utilize our provisioning tool, adding two (2) distribute software actions and one(1) reboot action under the system configuration section. The first distribute software action would be for the removal of older office version, next comes the reboot action and finally the install of o365.
We are running LD9.6 SP2 with component updates to 2015. I tried provisioning and was happy with it except for the fact that it will not continue if some user account does login. It is fairly important for the tasks to go on unattended. Yes the current bundled packages configured at Portal tasks do not continue the O365 install after the old Office is removed. So I am currently using two tasks - one to remove the old Office and the second to install O365. For the first task, I have the reboot setting in a separate Distribution & Repair setting. This usually works. I've been having some issues with the OffScrub.vbs files performing the Office 2007 removal if I separate out the Office 2007 in a separate task.
Thanks for the information. However, I tried the provisioning method and worked great. Except it will not be good because we would like to run these removals and installations on unattended computers.