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The main issue I have with password managers aside of being inconvenient and missing when you most need them: They are a bad single point of failure.
Your password manager is only a single point of failure if you only have one copy of the database. You do take backups, right?
Of course then the points of failure become the authentication credentials for that database, in the case of my keepass DB that is the key file and passphrase. The key file I have more than one copy of ferreted away (though obviously not stored anywhere connected to where the keepass DB is stored - keeping a backup of the key file in the same place as the DB would be silly). That leaves the passphrase, which is a set of random words that I do remember.
Using a set of four passwords for all your stuff does not solve one of the main reasons for keeping a password store. The main reason I have different passwords in keepass for every site/account/whatever (aside from one or two things that I might need to gain access to when I don't have keepass available) isn't that I want all my passwords so long and random that I won't remember them: it is that I don't want one hacked site to result in someone getting access to many of my accounts if said hacked account was on a system stupid enough to store passwords in plain text (or some easily compromised format, like SHA1 without a salt or with a salt that the attacker has also gained access to - see http://codahale.com/how-to-safely-store-a-password/ for why). You have no idea how your credentials are stored at the other end, so I err on the side of caution and assume it might not be secure.
Your password manager is only a single point of failure if you only have one copy of the database. You do take backups, right?
Of course then the points of failure become the authentication credentials for that database, in the case of my keepass DB that is the key file and passphrase. The key file I have more than one copy of ferreted away (though obviously not stored anywhere connected to where the keepass DB is stored - keeping a backup of the key file in the same place as the DB would be silly). That leaves the passphrase, which is a set of random words that I do remember.
Using a set of four passwords for all your stuff does not solve one of the main reasons for keeping a password store. The main reason I have different passwords in keepass for every site/account/whatever (aside from one or two things that I might need to gain access to when I don't have keepass available) isn't that I want all my passwords so long and random that I won't remember them: it is that I don't want one hacked site to result in someone getting access to many of my accounts if said hacked account was on a system stupid enough to store passwords in plain text (or some easily compromised format, like SHA1 without a salt or with a salt that the attacker has also gained access to - see http://codahale.com/how-to-safely-store-a-password/ for why). You have no idea how your credentials are stored at the other end, so I err on the side of caution and assume it might not be secure.