Out of curiosity: what do you work with? Asking since I’d like to move to OpenBSD as well, but several tools are not available. For instance, the company I work for relies heavily on Docker. :(
Yeah, that has been an issue at times. My team uses Docker, luckily it is only a few applications and it was easy to set them up to just be run directly. For heavy Docker usage though, that could be a deal breaker.
I also had to custom compile the pty4j and purejavacomm libraries to get the jetbrains IDEs to work to my satisfaction.