Thanks for continuing to add more information to help explain the migration process. We have separate Site and SUP Servers. We are planning to upgrade in place the Site Server from Server 2012 R2 to Server 2019. It's my understanding that the Site Server will not be able to communicate with the old SUP if they are running different O/Ses. Should we remove the SUP role from the separate SUP Server before upgrading the Site Server? Then we can either upgrade the SUP Server to Server 2019 or use a new Server 2019 machine (and start fresh). Is that correct?
We understand that SQL 2012 is EOL and we'll need to upgrade that as well. Does this need to occur immediately when running on Server 2019, or can it be done later (very soon after)? We're concerned about the length of time that the initial Site Server and SUP upgrades are going to require, and the DBA resources we will need to subsequently schedule.