@bkuhn @nik @Pandya afaik no, Debian upgrade processes are robust, but only if you don't skip upgrades: things that are used to migrate stuff forwards aren't always available in more recent versions of the packages.
and to be sure, I'd also take care to reboot between each step, just to be sure that the most recent version of systemd or similar stuff is compatible with the kernel that is running when it gets installed.