Creating a Smart Backup

I'm not sure of the best way to do this, be it with Time Machine, Automator or another 3rd party application, but here it goes:
I just got a new computer (MacBook Pro with Snow Leopard) and I would like to set up an automatic backup. I haven't trasferred any files in yet (they're all on my external HD), I wanted to see the best way to go about setting up my backup before moving the files in. Here's what I would like from my backup scenario:
1. Backups of the documents, music, pictures is pretty straight forward, just a smart copy kind of thing that automatically looks for what files are new/modified on my computer and updates everything on the external. I'm not sure if I can do this with Automator, or if one of the commercial apps I saw on the app store (DropSync, DirectorySync, etc)
2. Movies, however, is a bit more complicated. I have around 600GB of movies/TV shows, and don't have room for them all on my computer hard drive (computer is 750GB, external is 1.5TB). In fact, I would like to keep very few of the tv shows on my computer, only really the last one or two seasons. For example, on my external HD has the folder 'Breaking Bad', and within that is 'Season 1', 'Season 2', 'Season 3' and 'Season 4'. However, on my computer I still have the 'Breaking Bad' folder, but only have the folder 'Season 4' since I don't need seasons 1-3 on my computer. When I add a file to 'Season 4' on my computer, I would like the 'Season 4' folder on the external to be updated when I perform a backup/sync. However, this does not mean that the 'Breaking Bad' folder on my computer will be synced to the one on the external, just this subfolder. Can this be done? I'm assuming I'd have to go through and specify paths for all my folders, but there aren't that many shows so that would be ok to do for each season. I believe I'm out of Automator territory here, any suggestions on what I can do?
Also I don't think I would like to use Time Machine since I would like to be able to let friends/other computers take files off my external. I'm told with Time Machine it's not as simple as browsing the finder.

ChronoSync can certainly handle your needs just fine. To start, you can find out more about ChronoSync at the link below:
http://econtechnologies.com/pages/cs/chrono_overview.html
Now regarding your points:
1. ChronoSync can do this by setting up a schedule to run as frequently as you wish. ChronoSync does not support 'live syncing' where a file is synced as soon as it is modified, but you can schedule a sync to run as frequently as every minute.
2. I would recommend creating individual sync documents for each subfolder you wish to keep in sync between the two targets. You could then group your sync documents together in a sync container that could be scheduled and run like an individual sync document. You could also just use one sync document and exclude the items you do not wish manually to prevent them from being synced.
I may receive some form of compensation, financial or otherwise, from my recommendation or link.
<Edited by Host>

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Spinland wrote:
Then what CSound1 said: use CCC to clone your drive to another disk for safekeeping, then install Lion and enjoy. All of your apps will still be there after the upgrade.
Have you checked to make sure your apps are Lion compatible? This guide can help you find out:
http://fairerplatform.com/2011/07/are-your-apps-lion-compatible-how-to-check/
Hi Spinland
That is not what I said exactly ......
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Hi meatmailbox,
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