Not directly related, but the author mentioned Winston, which made me think: who are these people using Node.js that don't need log rotation? Winston doesn't have built-in support. The only logging library I've found that supports this without extra effort is log4node.[1]
Long-running programs will happily continue using the same file handle until they are signaled in some way to reopen the file path (usually in response to USR1 and HUP). See Nginx, Apache httpd, MongoDB, etc.
[1] https://github.com/bpaquet/log4node