Hi Joe,
WiFiLogger1 and WiFiLogger2 are the same as to running two programs at the same time (i.e. WL and WD) - won't work reliably!
Using either WiFiLogger 1 or 2 is fine for uploading to all the other services within WiFiLogger, and at the same time running a weather program, i.e. Cumulus does work using the program's Disconnect setting, but some data flow to the weather program will stop during the disconnect period but no resulting loss of data in the log. If the weather program is stopped and then restarted later the archive data will be downloaded from WiFiLogger like any other data logger.
Weatherlink Live without any other console or data logger will feed multi programs, i.e. 2 versions of CumulusMX or Cumulus and WeatherlinkPC, but does not have archive catch up at program restart unless you have the Weatherlink.com Pro subscription.
On another PC I have WeatherlinkPC and Cumulus but run one program only at the same time, and periodically (twice a month) I stop Cumulus to run WeatherlinkPC to update and save the WL data and then restart Cumulus.
I have run VirtualVP in the past so to run WeatherlinkPC and Cumulus at the same time, but that was not very reliable. I know several users here are using VVP to run more than one program but don't know if it is with WiFiLogger.
Enjoy,
Paul