I don't have an external HD to test with, but, essentially, I want to reinstall OS X. What I want to do is get a fresh copy of OS X after a reformat and rebuild my environment back up.
Most of my bookmarks, files, & multimedia are either on Dropbox or a NAS.
I need a way to recover important libraries like iTunes, iPhoto, & LittleSnapper including all the important metadata I've generated in the past year. I also need to recover some system-level settings like Keyboard Shortcuts, for example, I've set.
But, most importantly, I need to do all of this without recovering the state of the the operating system because that defeats the purpose of a reformat & reinstall.
However, if these methods fail, I will need to go back to the state of the operating system, do I have this option?
I'm probably making this overly-convoluted but I've been postponing a reinstall, however badly my system is in need of it, because I haven't been able to figure out the proper way of handling this is.
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How does Time Machine work?
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Time Machine makes a backup of your current state and then layers on top of that incrementally based on the changes on your machine between Time Machine backups (usually hourly if you have your drive connected all the time).
The type of restore you are describing is a major time commitment in my experience but the way I generally do it on my MacBook Pro is by using an identical drive to the one installed and making a clone of my internal drive to that one using a application called Super Duper (the basic version I use for this purpose is free here: www.shirt-pocket.com/SuperDuper/SuperDuperDescript...). Then I make sure to copy all the stuff I want in my new install (including libraries and settings) to a separate external drive. This way, if something goes wrong when reconstructing my new installation from the external drive I can just plug in the cloned drive and keep going from where I left off.
The type of restore you are describing is a major time commitment in my experience but the way I generally do it on my MacBook Pro is by using an identical drive to the one installed and making a clone of my internal drive to that one using a application called Super Duper (the basic version I use for this purpose is free here: www.shirt-pocket.com/SuperDuper/SuperDuperDescript...). Then I make sure to copy all the stuff I want in my new install (including libraries and settings) to a separate external drive. This way, if something goes wrong when reconstructing my new installation from the external drive I can just plug in the cloned drive and keep going from where I left off.
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First the Doctor hits some buttons, then it eventually fires up.......sorry i had to. While Time Machine is great for versioning type of backups, you really can't beat a bootable clone with something like SuperDuper. I personally use both, since they effectively solve 2 possible problems, file deletion and complete system malfunctions.
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Why don't you just use mobile.me, most of what you mention in your mail: email accounts, keychain, itunes, iPhoto, ... you can sync with mobile me. I only use timemachine to back up my files (including dropbox), and use mobile me for the rest.
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