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.
Using a local password manager, the file could get corrupted or it's not there when I need in in an emergency. Using a remote one, like LastPass, I risk my passwords getting compromised all at once (though maybe not in LastPass' case due to how their architecture works) or, again, not having access to them when I need them.
I have too many machines I'm using for various kind of work where I need different types of passwords. Too many to sync over my passwords and some not even my own, so I don't even want to sync anything there.
Now I have 4 strong passwords I use. One for banking/financial stuff only, one for work, one for "valuable" private accounts bound to my identity (this account here for example) and one for crappy sites I have to give a password to and I don't care if they lose it.
This way I'm not dependent on that password manager being available at a bad time.
The thought of not being able to log into some server people need me fix just because there's no 3g access in the data center or because an update to the password app on the phone didn't re-import the old data correctly is absolutely daunting to me.
Especially because these kind of failures feel more likely to me than one of my more secure passwords leaking out.
You are afraid that you won't have access to a strong password in case of emergency and therefore you choose to use a weak password? That doesn't make sense to me.
Wouldn't a better solution be to use a password manager and always have a current and working copy on you when you go out? I'm pretty sure it's doable and can be automated. Keepass + Dropbox being one possibility but you can make it more robust if you feel the need to.
Reuse of passwords is a much worse alternative than not being able to fix someone's server on the spot.
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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.
That's pretty much my strategy but I have about 30 passwords I reuse for different things. Like you I have 1 for "my weekend project" signups, 3 or 4 for social or other information type accounts, 1 or 2 for non-banking financial stuff eg. PayPal 1 for each main bank account or credit card, one for each main email, then a couple for communications services, the onto unix machines, root passwords, passphrases, SSL certificates, each of those has a pool of 3 or 4 passwords I re-use regularly.
I probably couldn't list them all but the idea is that they each have a common "threat level" and I'm generally able to get the password right for things I use every week first go, then it might take 3 or 4 tries to get it right for services I use less frequently but I rarely have to use the forgotten password link.
Using a local password manager, the file could get corrupted or it's not there when I need in in an emergency. Using a remote one, like LastPass, I risk my passwords getting compromised all at once (though maybe not in LastPass' case due to how their architecture works) or, again, not having access to them when I need them.
I have too many machines I'm using for various kind of work where I need different types of passwords. Too many to sync over my passwords and some not even my own, so I don't even want to sync anything there.
Now I have 4 strong passwords I use. One for banking/financial stuff only, one for work, one for "valuable" private accounts bound to my identity (this account here for example) and one for crappy sites I have to give a password to and I don't care if they lose it.
This way I'm not dependent on that password manager being available at a bad time.
The thought of not being able to log into some server people need me fix just because there's no 3g access in the data center or because an update to the password app on the phone didn't re-import the old data correctly is absolutely daunting to me.
Especially because these kind of failures feel more likely to me than one of my more secure passwords leaking out.