How so? You can use much the same techniques you would in Python, or you can deploy a .war to a bunch of application servers and achieve what you'd do with docker/kubernetes/etc. in a much simpler way. You've also got a much better chance of scaling up with a single instance and not needing to scale horizontally.

> the feedback cycle and general code velocity was much slower since we'd be on java 8 among other things

What's keeping you on Java 8? Major JVM version upgrades are much easier and safer than even minor Python upgrades. I'm not doubting your situation, but old version of one language versus new version of another is not really a fair basis for comparison.

> Plus learning spring or a Java ee framework is tantamount to learning a whole new language it wasn't worth the time then.

Sure. I'm not saying it's wrong to choose to stick with the technology you're currently using - there's definitely a cost to switching or learning something new. But it's worth being conscious of whether your technology choices are being driven by legacy constraints and whether you'd want to make a different choice on a green-field project.