Slightly different issue but I am part way through an upgrade from Whezzy to Stretch. After the upgrade to Jessie my (headless) computer failed to boot. After a struggle getting keyboard and screen it stalled after loading the kernel, probably a broken initrd file
It booted OK with the last Whezzy kernel but I am afraid to try to upgrade to Stretch with this suspect system. Problem is this machine is the interface between the LAN and the Internet so without it things are difficult ==John ffitch