What I understand is on the same laptop:
- If you use calibre (not portable) then both the wireless device and the content server connections work. We don't know whether it stops working if the USB drive is plugged in.
- If you use calibre-portable on the USB drive then the wireless device connection does not work. We don't know whether the content server connection works.
- We don't know whether connections work when using calibre-portable installed on the laptop's disk.
- We don't know if things will work if the firewall is disabled.
At this point it is impossible to debug what is going on. Providing answers to the "we don't know"s above will help pinpoint possible problem areas.
I might learn more if you
send me debug logs for both calibre and CC, but perhaps not. For example, debug logs won't tell me whether some antivirus is blocking connections, whether the firewall exception is actually being applied. It will tell me if calibre is seeing connection requests.
What does calibre's "debug device detection" report?
Do you "space issues" prevent you from running calibre (installed) with the library on the portable drive?