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I haven't heard about this problem in a long time. I was never able to reproduce this failure. Maybe a Catalina problem?
Anybody else here with this problem?

For the Log Station Info you need a xml subscription when you want to use qrz.com.
Make sure you have the Club Log databases loaded.
When you are new to RUMlog, read the manual very carefully.

You are using a macOS system function, this may not be useful. Export your QSOs and use an external app to print a document. The QSO Search window has a function to export a csv file. See above No! When you have (or have had) multiple personal callsigns, you should use one logbook file only. Enter ...

There are 16 user definable macro button available. Feel free to use two of them to power the radio on and off. See the full manual.

No

You can use:

• Apple Script - see Function Library
• UDP in the Flex Radio export format (N1MM Import)
• UDP in the N1MM export format

A Bluetooth LE module is still the best choice. iOS has no support for wired serial devices.

Reload the Club Log DXCC database. There was an error in the upload earlier this morning.

The polarity setting is for the real FSK input pin only. From the manual: FSK Transmit Polarity You can invert the logic level of the FSK IN line in FSK D mode using CONFIG:FSK POL. This should be used only with external keying via computer programs such as MMTTY; it is not recommended for use with ...

This results in sending reverse. You haven‘t mentioned, you use an external device.