...I agree that the code snip you shared works, but, it does not seem to work with the collection from my original post - trying yields a lot of:
Sort-Object : Cannot convert value "@{IP Address=x.y.z.99}" to type "System.Version". Error: "Cannot convert the "@{IP Address=x.y.z.99}" value of type
"Selected.VMware.VimAutomation.ViCore.Impl.V1.Inventory.VirtualMachineImpl" to type "System.Version"."
At line:3 char:11
+ $tester | Sort-Object -Property {[System.Version]$_}
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+ CategoryInfo : InvalidResult: (@{IP Address=x.y.z.99}:PSObject) [Sort-Object], RuntimeException
+ FullyQualifiedErrorId : ExpressionEvaluation,Microsoft.PowerShell.Commands.SortObjectCommand