After several failed attempts, and one not exactly successful one, at upgrading my kernel i have looked around and found that mine is not a one-off case, and this malady is rampant (mostly in Ubuntu/Debian). I am now in the process of reinstalling Jessie with the full intention of upgrading it's kernel later and was wondering if i could take some preemptive measures, or at least make a record of any relevant system data before and after the upgrade that i could refer back to if this happens again, and request a more advanced user to look at.

This may or may not be relevant but right from the time of installation and then for every boot, update and upgrade i get a notification of this missing firmware; Could not locate rtl-nic/rt18402-1.fw
Do you wish to install it from removable media?

and later,
possible missing firmware /lib/firmware/rtl-nic/rt189XX

I make it a point to install firmware-realtek along with firmware-linux after the first update on installation, that doesn't make any difference..