Several years ago I did a SBS 2011 to 2019 Standard migration. The problem, of course, was the Exchange portion. I got them over to Outlook 365 before even doing the migration. The problem was the autodiscover always wanted to look for the SBS 2011. I had to do registry entries and hacks to get Outlook working and pointing towards office 365. It was kind of a pain.
So now I have to migrate a SBS 2008 to 2019 Essentials. There are only eight workstations so a completely new domain would not be out of the question. How would you approach the migration and when would you move Exchange server to office 365?