Have tried with a previous customer (at their request and against my advice). In place upgrade path was 2008R2 > 2012 R2 then 2012R2 to 2016. Reverse imaged PVS back to standalone VM, uninstalled PVS Target, VDA, AV, SCCM client prior to upgrade. After upgrades converted back to PVS image with latest target/vda software and ran VMWare OS optimiser over it as a lot of the optimisation defaults changes from 2008r2 to 2016 including some network adapter config defaults. At the end the OS worked, PVS/VDA were ok and published resources could be launched, but I recall 2 of the older core LOB apps were completely broken. Tried reinstalls of them but broken they remained and a whole fresh image was eventually the only way forwards.