The Orion Upgrade Buddy does not help with reducing your overall downtime for the update. It does provide minimal polling while you are down for the upgrade. In order to minimize your downtime while upgrading multiple modules, I suggest to run them in the order suggested by our KB article and each time the Configuration Wizard starts, just cancel out of it until all the installers are done. For example, install NPM, cancel CW, install SAM, cancel CW, install IPAM (your last module) run CW. CW will then run the upgrade scripts for all the modules and reduce your overall downtime.
This is something we are looking at streamlining in the future, so hopefully the number of clicks can be greatly reduced.
KZ