> Do you really need the advanced features of AWS and Azure right now? Or would a simple virtual machine at a reasonable price be sufficient? That’s the main question here.

This is one of the more important points and why the point "The learning curve of a single server isn't so big, especially when compared to AWS" is sitting a bit wrong with me.

Sure, if you talk about 1 VM, I agree. And I wouldn't second guess doing this, at all. It would be my initial plan as well as long as I don't have to make any strong availability guarantees. And for this use case, I'd call AWS a bad choice. It's not a simple VM provider.

But once you start running e.g. a redundant postgres cluster for updates without downtime, the amount of stuff to know also grows, a lot. Suddenly you also need backups, tests of backups. And this is where AWS/the cloud allows you to save time, and treadmill time.