I have been out of the bitcoin game for awhile now and wanted to update my wallet for obvious reasons, also due to the alert keys warning I get(no idea what that is.) I just want to make sure that I don't mess it up and have to jump off a skyscraper

Make a backup or two (or 3) of the wallet.dat before doing anything, upgrading should be easy though. Also, be sure to scan for viruses.
This has some info about the message:
https://bitcoin.org/en/alert/2016-11-01-alert-retirement