Have you had a chance to look over this KB: https://jamfnation.jamfsoftware.com/article.html?id=122? Otherwise, if you have other questions that aren't addressed in that article, I would definitely suggest reaching out to Support so they can work with you to build a plan for your migration :)
Do you make nightly backups of your SQL database? In theory it would just be a matter of taking down the Mac Instance and importing the database on the Windows VM. The only issue you might run into is the server name if it's different. We use a load balancer so have the main server name in our Windows VDI instance.
In general such a lateral crossgrade should be easy ... just make sure everything is tuned well when you're done. (max_connections, Tomcat threads, etc.) make sure you're in good contact with your Tam though. I would also watch out for the windows installer...In the past it has caused some bugaboos. Flawless back ups are in order. Planning how high you want to scale is also in order. Perhaps with that many iPads, you might want to consider multiple Tomcat instances with clustering/load balancing. I would also highly recommend the CJA class...The entire class is devoted to scaling the right way.
@mstenson I would be interested in hearing more of your deliberations about this cross grade. A year and a half ago we were in the same boat... singles server JSS running on an under powered VM ...let's just say we found out the hard way that we needed to scale better. I now run a five-member cluster with load balancing that covers about the same device load that you have...it was the best decision we ever made. It just required me stepping outside my comfort zone and learning a whole bunch of new skills and utilizing our existing VMware infrastructure better.
@Kelly.Conrad Yes I have, that was the first thing I reviewed. I have already reached out to Jamf Support as well on the best and most precise way to go about this. @roiegat I am not sure, this will be a JSS we are inheriting. I assume that is definitely being done. We have access to the DNS records and we will definitely be modifying that record.
Have either of you done this? I am just trying to prevent any speed bumpss we may run into and make this transition as smooth as possible for the client.
Thanks for the responses!
We moved our JSS cluster from our local windows physical server for our master and Linux VM in the DMZ to self hosted Linux in AWS. As others said we just made sure we had our ports properly opened, everything tuned right, and then just imported a manual backup onto the new server and pointed the new web app to the database, and then just modified the DNS records to point to the AWS IPs and all was fine.