I've noticed that my Windows client is advertising multiple entries: root@fusion:~# nmblookup prodigy 192.168.0.55 prodigy<00> 192.168.56.1 prodigy<00>
It is doing this because there is a virtual network switch (VirtualBox) and it's accessible through either IP address. If I disable the virtual switch, only one entry is advertised, and ping resolves the netbios name. If I re-enable the virtual switch, ping stops resolving on Stretch systems. It looks like something changed between Jessie and Stretch - Jessie wasn't phased by the potential ambiguity, Stretch just gave up.