Hi,
The USB logger with the correct driver installed should work ok. And Weatherlink PC should also work.
Having that send a file everyday is not automatic.
But there are several other options.
Use a third party IP logger like WiFiLogger which is wireless from console so not directly wired to your PC. WiFiLogger can send a realtime.txt or wlfexp.json file. It can also send to Weatherlink.com and no PC required, but and can work with other programs on PC or RPi.
Use the Weatherlink Live device as your logger and which uploads to Weatherlink.com. This can be in addition to your console and USB datalogger, or a replacement to both, so saving some purchase cost. But it does require a paid Weatherlink.com subscription in order to see historical data on Weatherlink.com. It does not need a PC.
Instead of running Weatherlink PC program use a third party program like CumulusMX (free) and that, among many other things, saves data in .txt format. Your existing console/USB logger will work with this. Why don't you want to leave the USB logger connected to your PC.
Enjoy,
Paul