I'm little puzzle on if I can or if I should re-deploy ArcGIS Enterprise if the end goal is to migrate and upgrade. Currently, our small agency (only 2 people using GIS) is running on ArcGIS Enterprise 10.6.1 on a Windows Server 2012R2 VM machine with a little SQL Express SDE. We're considering migrating it to Microsoft Azure cloud. Is this something we should start from scratch and use the deployment method or use the WebGIS DR Tool migrating method? Such as backup and restore to WebGIS DR at the same 10.6.1 release, and then upgrade to 10.8.1 in the target environment - MS Azure cloud?
Personally, I would say it depends on how much content you have to migrate in the first place. The more content being move, the better WebGISDr will become. If it's possible, I would recommend upgrading in place to 10.8.1 then migrating. WebGISDr is more robust in later versions, and there are less issues likely to come up.
If there is only a few items, that can easily be recreated, it may be easier to start fresh in MS Azure and have two browser windows open to get the content looking the way it needs to.
I agree with Reese. I would personally migrate the content using ago-assistant or Python API for ArcGIS. I would first start with an inventory and the practicality of using WebGISDR to move your content. The time to create a full backup of ~40 gigs was 37 hours in 10.8.1. I do not know how stable webgisdr is between two versions of Enterprise and the implications that it might have when importing into your 10.8.1 site.
I know one for sure advantage of republishing content is the availability of dedicated or shared instance pools when Publishing from ArcGIS Pro. I would imagine if you use WebGISDR to restore map services then you will bring over the default settings in 10.6.1.
I did a complete redeployment last summer when moving to new servers on-premises and went from 10.6.1 to 10.8. A big factor in my decision to do a redeployment was during every single in-place upgrade I did over the past few years I encountered problems that introduced issues into our deployment. I did not want to risk carrying those issues over to the new servers. We have many services, maps, and apps but for me the time spent redeploying was well worth it because all of our random issues went away.
Also keep in mind, if you are switching from Windows Server to Linux when you move to the Azure you will not be able to use the WebGISDR tool to restore from a backup.
Thank you all for your reply, suggestions and recommendations. Very appreciate it! After gathering all your and other info, we've decided to start fresh, upgrade and re-deploy to ArcGIS Enterprise Standard 10.8.1 (currently just Workgroup Standard 10.6.1) to MS Azure. We will still need to look more into it and plan it out, but would the "Cloud Builder v2 for 10.8" be a good start? Thanks again!