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Lets assume I have access to the windows machine.

I want to grab raw info about logins/hashes from both system and installed apps, dump and analyze it later.

I could manually dump things like SAM database, saved passwords preserved in browser, im client, etc, but this seems to be rather time-consuming and I need to know what exactly to dump for every specific app.

Is there a way to automate the process? I.e. I'd like to run process that will search the system/apps to see what is installed and grab sensitive files, so I could try to crack them later.

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Sure there is, it's called scripting. – Lucas Kauffman Sep 12 '12 at 7:22
There's a ton of spyware that does this. They usually go after product keys in the registry. I analysed one a couple years ago that had key extraction routines for a few hundred popular applications and games. – Polynomial Sep 12 '12 at 7:31

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Use metasploit with meterpreter scripts to invoke post_ modules.

http://en.wikipedia.org/wiki/Metasploit_Project

http://www.offensive-security.com/metasploit-unleashed/Writing_Meterpreter_Scripts

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