I've got a user in the community with the same issues which were reported by cobbkris.
Screenshots would show the same pictures as posted the ones posted by cobbkris. That's why I don't upload new screenshots.
He is using SRT V2.22, of course.
First of all I checked his rF2 installation in order to check, if he placed all of the 3 files correctly. Location of the files is correct.
I turned off his anti-virus programm (Avira) and Windows firewall. Additionally I added SimRacingTools.exe to the list of programms in the firewall which are allowed to cummunicate and enabled it for all kinds of networks (home and public).
Finally I made him execute SRT and rFactor2 (non-Steam version) as Administrator.
Although we tried all these actions together, he is not recognized as connected to our league's server (see cobbkris's 2nd screenshot).