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. :(
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.
I also had to custom compile the pty4j and purejavacomm libraries to get the jetbrains IDEs to work to my satisfaction.