I agree that it's a good idea to keep at least one older kernel that you know
that you can boot the system with but I see no point in keeping several
3.13.x versions installed. Personally I try to run the very latest (stable)
kernel with the latest long-term-support version as backup (both in the 4.x
series). I also try not to upgrade both of these at the same time.
Do i really have to remove them manually in Synaptic?
Yes, I believe so. Maybe Trisquel doesn't auroremove kernels to be on the
safe side, because the consequences are so bad if, for some reason, you don't
have a working kernel to boot with any linger.