So I created a batch file with the commands below:
REM Remove files older than 14 days
forfiles /p "C:\my dir" /s /m *.* /c "cmd /c Del @path" /d -14
And then I ran Task Scheduler and set the batch file to run daily and delete files older than 14 days old. That lets me keep plenty of vids, while never filling the HDD (which actually caused the CMS to crash, ha), and I don't have to do anything manually. Hope this helps someone in the future.