I've run a few (failed) projects in the past as a solo founder as well, and my single most important learning is to keep things simple, specially when it comes

I've run a few (failed) projects in the past as a solo founder as well, and my single most important learning is to keep things simple, specially when it comes to infrastructure. You want something which is super easy to deploy, rollback, and debug. Docker in itself is not necessarily easier or more difficult to manage - that depends on your orchestration solution. If you're using it to deploy to Heroku, that's probably fine. But if you intend to use something like Kubernetes or AWS ECS, I'd rather not to as they come with significant overhead and lots of moving parts. I'm currently managing a Kubernetes cluster in GCP for a big client, and I couldn't be more convinced that this is definitely not the kind of solution I'll use for my own projects. Finally, although it goes contrary to what is usually recommended, at the beginning I'd personally avoid Terraform and/or AWS CloudFormation as well, as they come with their own overhead and sometimes make small changes more difficult. And it's a context switch.