Hi Ned,
Don't have $500 to gamble on the fact Microsoft may decide this is a bug or not i'm afraid.
We are just going to have to go with manually setting the IP address ourselves but In any case it definitely appears to not work between 2008r2 and 2019 I have tested a 2019 to 2019 migration and it works fine. With a different 2008r2 to a different 2019 server i also see the same issue (version 1.83.2 of the SMS service and 1910.2 of the admin centre)
Including below incase it helps you anyway.
for the 2019 - 2019 after the events setting DNS we then see 2 events about the gateway and creating the IP address on the destination server
05/12/2020-16:04:43.767 [Info] Adapter 'vmxnet3 Ethernet Adapter' on 'xxxxxxx': EnableWINS(False,True,,) [d:\os\src\base\dms\proxy\cutover\cutoverproxy\NetworkInterfaceMapper.cs::EnableWINS::950]
05/12/2020-16:04:43.782 [Info] Adapter 'vmxnet3 Ethernet Adapter' on 'xxxxxxxxx': EnableDNS([xxxxxx,xxxxx], [xxxxxxxxx]) [d:\os\src\base\dms\proxy\cutover\cutoverproxy\NetworkInterfaceMapper.cs::EnableDNS::1036]
05/12/2020-16:04:43.876 [Info] For IP '1.2.3.4' on source computer the gateway is '1.2.3.254' [d:\os\src\base\dms\proxy\cutover\cutoverproxy\NetworkInterfaceMapper.cs::AddStaticIPsFromSource::1112]
05/12/2020-16:04:43.876 [Info] Creating IP '1.2.3.4', prefixLength '16', gateway '1.2.3.245' on adapter 'vmxnet3 Ethernet Adapter' on 'xxxxxxxxx' (interface index 3) [d:\os\src\base\dms\proxy\cutover\cutoverproxy\NetworkInterfaceMapper.cs::AddStaticIPsFromSource::1113]
for the 2008r2 --> 2019 we see the events where it sets the wins/dns and then there are no no events logged regarding setting the ip address on the destination server.
05/12/2020-16:59:05.237 [Info] Adapter 'vmxnet3 Ethernet Adapter' on 'xxxxxxxxxxxxxx': EnableWINS(False,True,,) [d:\os\src\base\dms\proxy\cutover\cutoverproxy\NetworkInterfaceMapper.cs::EnableWINS::950]
05/12/2020-16:59:05.237 [Info] Adapter 'vmxnet3 Ethernet Adapter' on 'xxxxxxx': EnableDNS([xxxxx,xxxxx], [xxxxx]) [d:\os\src\base\dms\proxy\cutover\cutoverproxy\NetworkInterfaceMapper.cs::EnableDNS::1036]
05/12/2020-16:59:05.300 [Info] Start cutover operation async. [d:\os\src\base\dms\proxy\cutover\cutoverproxy\CutoverService.cs::StartOperation::55]