Now, I'm comfortable with TeamCity, Octopus Deploy, Azure (a ton of hosted services), PowerShell, and a host of other tools.
I've set up bunch of HipChat integrations so we know exactly where in our pipleline a particular build is (code pushed, dev build/deploy, and promotions to various environments), if there was a problem with a unit test run, if there were problems with integration tests, and if there are problems in dev/staging/production with our actual live running code via HipChat integrations with our structured log processing server.
There are good tools out there and they're pretty usable - just maybe not at your price-point of free for your environment. I went from 0 to 1-click whole-environment deployments in just over a year.