What is the best way to manage my hard drive?

Background - I have a 13" MacBook Pro with 250GB hard drive and recently I have had to delete or migrate files to external HDs to gain space. I spent last night doing just that. I also have two EHDs - a 2TB My Passport and a 3TB Seagate GoFlex Home WiFi capable. I do my backups to the SeaGate using Time Machine. My issue is that I currently only have about 38 GB available on the hard drive after making the moves last night.
I'll call this what it is - an ugly baby. In order to make room, I moved files to one or both EHDs so now I have multiple copies of my stuff but no organization. So a couple of questions...
1. How can I effectively and efficiently get my internal hard drive down to only about 100GB be used? What I would like to do is reduce the files and folders on my mac to the pictures and basic document files in my documents folder. I think I can do this by moving all music to an EHD which would free up more than 100GB on my macbook. I just am not sure how to do this and not affect my iPhone's iTunes etc.
2. I want to back up my info to a cloud, specifically pictures and important docs... I would be introducing a third way to get disorganized. What do I need to do to stay ahead of the curve.
Thanks in advance...

Upgrade your MBP's internal boot drive to something larger, 250GB just doesn't cut it.
A 2010 machine, I wouldn't bother with the expense of a SSD, a 7,200 750GB or 1TB should do nicely and you can install it yourself or have a local geek do it.
You might as well max the RAM too, if your in AppleCare it won't violate it as long as nothing is broken.
Carbon Copy Cloner is the preferred method to clone your entire OS X + Recovery HD partition (no BootCamp, use WinClone 3 for that) to a external GUID OS X ext J drive, hold the option key and boot from the clone, then reverse clone onto the new internal drive.
OtherWorld computing, MacMall and Crucial.com are recommended for compatibility, videos and what not.
Install/upgrade RAM or storage drive in Mac's
don't forget to clean the cooling fins behind the fans, they get clogged with dust and overheat the machine.

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