These problems would basically all go away if you used a process monitor to handle setting up the environment for the server process, including fds 1 and 2, and

These problems would basically all go away if you used a process monitor to handle setting up the environment for the server process, including fds 1 and 2, and then just let it log to stdout or stderr. Any halfway-decent process monitor can do this, and most of them can handle log rotation as well.