The solution to the automated deployment in Azure is use ElasticBox.
I will skip the details of all the configuration options for Azure supported by ElasticBox, as they are detailed in the documentation section: http://elasticbox.com/documentation/deploying-and-managing-instances/using-azure/.
You only need to create a box (abstraction unit that ElasticBox uses to define the installation and configuration of the deployment of a service or application in any cloud) that takes care of the steps you need to be automated. So finally you will deploy the vm with near no manual intervention, just one click or a command with some parameters.
A box includes the variables necessary for your deployment and your scripts (In this case probably PowerShell, but they could be bash, python, perl, java, etc.)
When you deploy the box you create to deploy your application, ElasticBox will:
Create a Cloud Service or VM. (ElasticBox takes care of provision the vm in your Azure provider, or any of your preferred cloud provider).
Install a specific build of the product (as a standalone exe or Windows service, not IIS) -> This should be your install event script.
Tweak the configuration files(s) -> This should be part of your configure event script.
Set up user account(s) -> This should be part of your configure event script.
Run the exe/service -> This should be part of your start event script.
ElasticBox has a command line tool that enables to do VM deployments of your boxes and also you can manage your deployed vms with it: https://pypi.python.org/pypi/ebcli
It also support automatic termination of the vm after a custom time value.