HI
7 Will this delete everything on the VM?
no. but we must backup our wse2019 app server and wse2019 fileserver first in order to avoid unexpected condition.
8 "Can't we use the AVMA keys to activate the Standard OS on VM2 and VM3?"
yes, we can use w2019 standard AVMA keys to activate w2019 standard VM guest in w2019 Datacenter Hyper-v host but i am not sure if you can convert wse2019 retail channel to w2019 standard AVMA channel by using w2019 standard AVMA key successfully. but I am sure you can use retail w2019 standard product key to convert retail wse2019(retail channel) to w2019 standard(retail channel).
for your condition, I also think when we do conversion option, we need to keep channel the same .I guess we can try below solution. install new wse2019 vm4 by using your wse2019 retail iso in your w2019 datacenter hyper-v host to simulate it.
solution 0:wse2019(retail channel) --w2019standard (VMA channel)
solution 0 is out of my guess solution, but there is no offical document to say no for AVMA condition .you can install new wse2019 vm4 by using your wse2019 retail iso in your w2019 datacenter hyper-v host and not activate vm4 by using retail key then using w2019standard AVMA key to convert and activate it.
1)slmgr /ipk <w2019 standard AVMA key> auto activate by using w2019 standard AVMA key
2)slmgr /dli to check the license status
solution 1:wse2019(retail channel) -->wse2019(volume kms channel)-->w2019standard(volume kms channel)-->w2019standard(VMA channel)
install new wse2019 vm4 by using your wse2019 retail iso in your w2019 datacenter hyper-v host,it will simulate how to convert to vm2 or vm3 to w2019standard.
1)slmgr /ipk <wse2019 kms channel key> ( convert to wse2019 volume kms channel )
2)dism /online /set-edition:ServerStandard /accepteula /productkey: Product Key (where Product Key is the kms channel w2019 LTSC standard key )
3)slmgr /ipk <wse2019 AVMA key> auto activate by using w2019 standard AVMA key
4)slmgr /dli to check the license status
solution 2:wse2019(retail channel) -->wse2019(VMA channel)-->w2019standard(VMA channel)
it will simulate how to convert to vm2 or vm3 to w2019standard.
1)slmgr /upk to uninstall retail product key
2)slmgr /ipk <wse2019 AVMA key> auto activate by using wse2019 AVMA key
3)dism /online /set-edition:ServerStandard /accepteula /productkey: Product Key (where Product Key is the w2019 standard AVMA key ).
4)slmgr /dli to check the license status
there are reference documents link
Automatic Virtual Machine Activation (AVMA) in Windows Server 2016
http://woshub.com/automatic-virtual-machine-activation-avma-in-windows-server-2016/
Server 2019 - Unable to do in place upgrade with AVMA keys
https://social.technet.microsoft.com/Forums/ie/en-US/8c2683e9-c515-4f9c-84f4-e1c7c6c50bad/server-2019-unable-to-do-in-place-upgrade-with-avma-keys?forum=winserversetup
Upgrade and conversion options for Windows Server 2016
https://learn.microsoft.com/en-us/windows-server/get-started/supported-upgrade-paths
KMS client setup keys
https://learn.microsoft.com/en-us/windows-server/get-started/kmsclientkeys
Windows Server release information
https://learn.microsoft.com/en-us/windows-server/get-started/windows-server-release-info