[balabaster]

It depends very much what your tech stack looks like, but I use Git, CircleCI and Octopus Deploy to Azure for my stack. It's cheap in terms of maintenance and because I know them all like the back of my hand it's quick and easy for me to set up.

As for rollback, I don't really use rollback. I have a roll-forward strategy. My DB deployments are migrations and so long as there's no data-loss caused by a migration (my migrations are always backwards compatible with the previous version) there's no need to roll back. Azure brings point-in-time restore which can be triggered if necessary.

I think the key is like with anything. There's a learning curve on your toolset. Once you've overcome that hurdle and you know to set up automation for everything from the outset. You build your pipeline shell. You never do anything manually. If you need infrastructure of any form, it's always code-first, included in source control and done the right way. Never do anything manually and rely on your automation to carry you. It seems labour intensive up front, but once you're there, it's sustainable.

It takes discipline not to cut corners. The minute you start to cut corners and get lazy is the path leading to your doom.