Yes, I used a single uberjar for the first year or so, but then it got a bit more involved, because of delivery optimizations (nginx, brotli, precompressed files, versioned immutable static content with infinite cacheability, etc). So these days it's an uberjar (AOT-compiled) plus a bunch of files, essentially.

The servers are managed using ansible, and I also have a terraform setup for quickly spinning up a development cluster "in the cloud". Ansible takes a list of servers either from a static file or from terraform.