I'm writing up this post in hopes to help anyone trying to upgrade their Orion platform from 2020.2.6 or earlier to the new 2022.4. During the upgrade, we ran into several problems, especially with the new HCO licensing. The main issue we found is that the older platform does not have the "Hybrid Cloud Observability" license type in the license manager which will make it so you cannot manually activate the license. We also could not run the installer because we received an error that we did not have a valid license to upgrade the products we already have, and since the new HCO license didn't match the old module activation keys it would not let us proceed.
SW Support suggested we "Force expire" all of the licenses via CMD on the Solarwinds server. You just need to make sure you're in the licensing directory on the cmd shell and type the command /ExpireAll, it will give you a little warning saying this will deactivate all the licenses, select yes and then re-run the installer. The default directory for the license store is C:\Program Files (x86)\SolarWinds\Orion\Licensing, ours was on a D:/ Drive so make sure to check your other drives if you can't find it on C:/
Finally, this allowed the installer to complete, but we ran into another error with the Configuration Wizard. Specifically, it kept failing around 98% with a message of "Verifying that the SWIS service is available FAILED". We looked through many THWACK posts and official support memos and tried most of the workarounds, but none seem to work. I then found one workaround that said to manually activate the license through the web application portal, the only problem though is since the Config Wizard did not finish, we could not access the web portal. However, since the installer finished I checked the License Manager again and found that the new Observability License type was available. I clicked "Activate" and selected the option that says "I don't have access to the internet" and was able to get the correct Unique Machine ID to take to the customer portal and generate a manual license. I then uploaded the license to the SW server via a shared drive and activated it in the license manager. The license successfully became active and we re-ran the Configuration Wizard. This time the CW was completed successfully. We did have a few weird things after completion, one of them being our previous DNS entry no longer worked for HTTP and we had to use HTTPS:// "server name" to access the web portal.
Hopefully, this helps someone save time as it took about 5 hours for us to successfully get everything in place.