I've recently begun using Keepass for my personal password management.
I am setting it up to sync between my home PC, work PC and mobile device using dropbox.
I'm going "all the way", and have changed my passwords to 32 character mixes of letters, numbers and special characters. Even for stuff I commonly use, like my primary email, I've changed to a long complicated password.
My one concern is a Total Loss Scenario.
If in some bizarre twist of fate I were to lose my home PC, my workplace PC and my iphone all in one fell swoop, I would have no idea how to login to any of my accounts - email, dropbox, etc. Thus making my ultra secure password database file inaccessible, even to myself!
Should I have one "entryway" for myself - setting my personal email or dropbox password to something that is complicated, but that I can commit to memory?
Any other suggestions on how to be both ultra secure, and to be safe from cutting myself off from my own passwords?
edit: Some people even suggest keeping an unlabeled holdout password written on a card in my wallet.