bray's terminal scans for COM-Ports on startup. But is unable to re-scan if the software is already running. There is a scan for COM-port-function but you only see a message
"access denied"
I assume (= not knowing) this is caused by the age of the software 2013
So the feature is
always successfully re-scanning the available com-ports
start a new logfile once per hour, once per 24 hours
I imagine that an emulator with a script language may well be able to do what you describe. Many, many years ago I used a terminal emulator named Reflection 4, which has a script language, albeit using what amounts to BASIC, to run performance tests on a mainframe system and it did all that I needed and more