I'm seriously considering the use of LastPass toolbar or something similar. I'm wondering if there is any history of these things crashing and losing all your passwords.

I've used LastPass for several years. Just the free version.

I completely trust the security of my passwords to it and, in fact, there are several sites that I don't even know the passwords for!

I also use the toolbar (both in IE and Firefox) and have had no problems with it. In my Firefox setup I have many, many extensions so if there were to be some sort of conflict or problem with the LastPass toolbar, I'm sure I would've experienced it.

I highly recommend this password manager. I sound like a shill for them, but I assure you I am in no way related to them.

Hope this helps,
WallyH