Hmm wait_for is a python module.
waiting for the port will work fine as that will presumably be happening on the ansible controller, rather than remotely on the machine you are trying to access.
If only waiting for a file will do then you could try using the fetch module to pull the file back you want to collect (fetch runs against windows hosts), then examine the file on the ansible controller.
Would likely need to be wrapped in a block / rescue / always block - see
http://docs.ansible.com/ansible/playbooks_blocks.html, and you might need to start off by waiting for a certain amount of time to avoid having to have multiple blocks to retry, but it might be enough to get you going.
Hope this helps,
Jon