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.
My desktop machine runs OpenBSD (after getting off of OS X) but I have a few headless Linux machines for things that only run on it.