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Upgrade problems (wheezy->jessie)

I seem to need to upgrade to Debian stretch to install my printer as
it needs hplip 3.16.11, ad I was running wheezy.  I understand this
needs to be done in two stages, wheezy->jessie->stretch, but I still
need advice as I cannot find out the solution to my problem.

I tried upgrading from Wheezy to Jessie using apt-get upgrade and
apt-get dist-upgrade as the instructions said.  All seemed OK until
disaster struck when the Jessie failed to reboot.  As the computer is
headless I had to dismantle it all, loose the internet to the entire
LAN, and find USB keyboard and dvi cable for screen.  Eventually
discovered that the kernel installed with Jessie did not load, but the
previous kernel did.  An hour or so thinking and I managed to get
autobooting to work so re-installed with internet and hidden
location.... , and eventually communication resumed.  But...

1) Why will vmlinuz-3.16.0-4-amd64 not load (says loading and the does
nothing for over 30mins) when vmlinuz-3.2.0-4-amd64 does load?

2) Is it OK to run with the older kernel?

3) More importantly will it happen on Jessie->Stretch as climbing up
to dismantle the local net is hard (I have a balance issue) or is
there a way of testing before rebooting?

Any help very welcome

==John ff