The latest jailbreak survives all known updates.
(But do make sure your jailbreak is at least JB 1.13.N so it includes the "gandalf" component.)
That said, my Kindle Touch hasn't been updated for the last couple point releases. As was suggested above -- if it ain't broke, don't fix it.
Even if I can just reinstall my hacks, it is still an unnecessary pain to redownload and install them all. It is a complete waste of a few minutes.
...
I use the update.bin.tmp.partial/ trick.