If you are a vertical market solution provider then this pattern will appeal to you.
Single server variation This document covers upgrading several customer applications that are all running on a single server. If you have many servers to upgrade then you will need to repeat this process for each server for now. We have multi-server target support on our near-term roadmap for OttoDeploy.
You want to upgrade several customer applications that are all running on a single server with the same "new version" of your application.
You can use sub-deployments to deploy the same version from your dev server or from a "release build" to each of the application instances running on the server. Each sub-deployment can be setup to use the specific file names and file options for each customer.
Since each sub-deployment is atomic, if one of the sub-deployments fails then the remaining sub-deployments will not be affected, unless you use the abort remaining option feature.
You will need to turn on the "Advanced options" in the deployment settings to use the sub-deployments and abort remaining sub-deployments features.