Someone takes my Mac and is able to guess or otherwise break my login password. I am still protected for my login keychain by a second, stronger password.
As I said before, even if your login keychain uses exactly the same password as your login password, resetting the login password will not help an attacker break into that keychain. The attacker would have to guess your login password to get access to that keychain. Of course, if you've chosen such a poor password that someone could guess it, you can hardly call that a system vulnerability!
however, being mac-savvy, the thief opens keychain access and selects my
*System* keychain and unlocks it. It asks for a password and the thief enters my login password.
Again, this relies on the thief knowing your login password. However, I'm not sure what the effects of resetting the login password would be on the
System keychain. I would think that the same thing would apply and you'd lose access to those passwords. But since this keychain has a different purpose than the others, maybe not. The only way to know for sure would be to test it.
the System Keychain only contains passwords which are needed across all users, but these include the network and time capsule passwords which are pretty critical...
That's assuming that resetting the password gives access, which may not be the case. Even if that is the case, those passwords are not really critical... choose a unique password for these things that you don't use for anything else. Your scenario of having someone steal your laptop yet stay on-site and mess with your Time Capsule is a bit silly. The thief already has your machine, so there's nothing on the Time Capsule that they won't already have.