I just reproed the same issue for you:
Latest Model goes to NO status immediately once you connect your Azure Devops pipeline to this particular VMSS.
In general scenarios , if any changes are done at the VMSS config end and if those are not propagated to the instance level - that's where the Latest Model will show as NO - which also indicates that those instances needs to have the latest changes which are applied on the VMSS level.
To make to YES , you need to select the instances & click on Upgrade !!
Couple of options which I was thinking to use the same instances with name:
-> In the Azure Devops pipeline , you can unselect the option of "Automatically tear down virtual machines after every use " , so that those VMSS instances will not get deleted !
-> Try to use the VMSS with Flexible more
Will continue to do more research for you , but you can start with those options for now...
Regards,
Shiva.