Hi Kelsey,
I don't think you are missing anything really.
Your geodatabase maintenance strategy looks good, I see no issues there. The only question I have is, why are you deleting the versions? Are you going for a full compress each time you run this?
I ask because it goes into your second question. Having to re-register all of those child version connections with Server is expected. See this note below that we include on our page on the topic:
"If the database you register contains a versioned geodatabase, ArcGIS Server accesses the version of that data present in the geodatabase version you set for the connection file. If you want ArcGIS Server to access different versions, you must register separate connection files to connect to these geodatabase versions. For example, you may need to register one connection file that accesses the Default geodatabase version and one that accesses a child version."
About registering your data with ArcGIS Server—Documentation | ArcGIS Enterprise
So given that, it seems like deleting the versions each time may not be the best way to proceed. There is a way to get a full compress done without deleting the versions if that is the goal. But getting a full compress done each time you do this is also not necessary.
- Reconcile and post all child versions to Default
- Re-reconcile all child versions to Default (without posting)
- Save edits
- Compress
Doing the above will also get you a full compress if that is the desire and also not delete those versions which means you won't need to re-register databases with Server.
Jonathan