I would recommend that you read this if you haven't already.
https://www.amigaforever.com/kb/14-109Also, USB to SER adapters can be problematic, especially when interfacing to older hardware on the SER side.
On older hardware the serial port hardware is often looking for more significant voltages than the USB to SER adapter can produce. If I remember correctly, the Amiga 2000 was designed for +10 / -10 VDC on the serial port. See this
https://en.wikipedia.org/wiki/RS-232Sometimes you can get lucky and the USB to SER will work cause the levels are right on the edge of what is considered a valid level. Other times it won't work no matter what. And still other scenarios like works sometimes and then stops. An additional load on the computer power supply can cause the voltage to dip just low enough that the RS232 signals drop below the "valid" levels. For example, the RS232 works when the floppy drive is not running but doesn't work when it is running.