Watchman Monitoring supports Mac and Windows OS. Installation on Windows run on a Mac via Bootcamp is supported.
Installing the monitoring client on OS X and again in the Mac's Bootcamp environment would result in two independent computer records, each showing the same serial number.
A natural fact would be that only one OS's agent could perform its hourly runs at a time, depending on the currently booted OS.
of course only one side can report at a time
so, the other record would be considered stale if they don’t switch every 7 days (at least)
The Windows side would report issues it found, the mac would report issues it found too
Things like the hard drive getting too full.. would be reported as two issues on two computer records
If the computer is used mostly in one OS, you’d want to uncheck the other record’s “notify if missing” option in the /edit page for that computer record.