So many problems... My MacBook Pro is full and I'm terrified I'm going to lose all of my photos and music.

Question

Where to even begin with the problames I'm having!?  I have a MacBook Pro  OS X 10.5.8, an iMac OS X 10.5.8, a 500GB Time Capsule, and an iPhone 4s. I know just enough about all of them to basically get myself into trouble... And It seems I have done a really good job at messing everything up!
I bought the iMac and Time capsule together in 2008.  The Time Capsule didn't work properly for backups from the start (although it functions great as a router for my home network), and I spent several hours on the phone with applecare, took it to the Genius Bar etc., and it still has not ever worked as a continuous background backup.  I did somehow manage to acquire one backup of the iMac with the TC before I did a reboot of the iMac a couple years ago.  I can access the backup, but im not sure if the backup is actually on the time capsule or if it is saved on the HD.  Furthermore, I have another backup (pretty sure it's a partial backup) from the MacBook Pro, and I don't know where that one is actually stored either. The Macbook Pro is so full that it is not functioning properly and i'm afraid it will die.  I have subscribed to both Backblaze and Crashplan... The initial Backblaze backup completed on the MacBook, but I don't even have enough diskspace to download Crashplan.  I need to get both Macs backed up to an external hard drive  and I would like to save the backups I already have.  I am also trying to start my own photograghy business, so I would like everything setup so that I can manage photos from both Macs and be condusive for storing and editing loads of photos. So here are my questions...
1. Can I (and should I) back up both Macs to one external hard drive?
2. Can I use the Time Capsule to route wireless continuous backups from the MacBook Pro to the external hard drive or would I need to have it wired every time?
3. Which external hard drive would be best for my situation?  Would a RAID be best or is that overkill?
I am considering this one in either a 2TB or 3TB:
http://eshop.macsales.com/shop/firewire/1394/USB/EliteAL/eSATA_FW800_FW400_USB
4. Once everything is safely backed up, what is the best way to get my HD space freed up?
5. How do I set up the drives so that I'm not using all of my internal HD space for photos and music?
6. When I have enough space to upgrade to OS X Lion, will the cloud make a difference with how my photos are managed?
I know this has been extensive, and probably frustrating to those of you who know what your'e doing... Thanks so much for your time and patience!!

Answer 1

1sweetORnurse wrote:
1. Can I (and should I) back up both Macs to one external hard drive?
You can (if it's large enough), but see below.  You should probably create a second partition on the drive for the second Mac. You can also back them both up to the TC.
2. Can I use the Time Capsule to route wireless continuous backups from the MacBook Pro to the external hard drive or would I need to have it wired every time?
There are several options:
Since you have an iMac, by far the fastest, easiest, and most reliable way to back it up is to connect an external HD directly to it.
It's slower, but you can also back it up to the TC.
The laptop can be backed-up to the same drive as the one connected to the iMac, over your network.
Finally, although I wouldn't recommend it in this case, you could back up either or both to an external HD connected to the TC.
3. Which external hard drive would be best for my situation?
Most likely, a good quality external HD. If you're going to use Time Machine, see Time Machine - Frequently Asked Question #1 to be sure you get one large enough. 
Would a RAID be best or is that overkill?
In most cases, overkill.  For redundancy, duplicate backups made on a separate HD, with a different app, is a bit safer than a RAID.  See FAQ #27 for some suggestions.
I am considering this one in either a 2TB or 3TB:
http://eshop.macsales.com/shop/firewire/1394/USB/EliteAL/eSATA_FW800_FW400_USB
That link doesn't work for me -- it redirects to the main page.  I have one of their Mercury Elite Pro multi-interface drives, and it works fine.  Most anything they sell will be fine, as long as it's large enough.
4. Once everything is safely backed up, what is the best way to get my HD space freed up?
Even before you do that, check for hidden large stuff on your Mac that you don't need.  See Where did my Disk Space go?  There may be some things there that will gain you a few GBs, at least.
Also, obviously, delete anything you don't need, especially video, photos, music.
Do you have duplicates of the same files on both Macs?  If so, deleting one might save a lot of space.
Then, you need to consider where you're going in the future.  Backups alone won't gain you any space -- the essential part of a good backup strategy is to have (at least) two copies of everything important in (at least) two different places.
So most likely, you need to move some big stuff, such as your iPhoto and/or iTunes libraries, or a large video collection, onto a different external HD, and let Time Machine (and/or other backup app) back it up along with your Macs.
5. How do I set up the drives so that I'm not using all of my internal HD space for photos and music?
Be sure to format them for a Mac (most come pre-formatted for Windoze).  See #1 in Using Disk Utility.
Depending on what kind of data you want to move, you can just drag and drop, then delete.
And/or see:
Moving your iTunes Music folder
Moving your iPhoto '11 Library
Moving iMovie '11 footage to another drive
6. When I have enough space to upgrade to OS X Lion, will the cloud make a difference with how my photos are managed?
I don't think so.  
What's on your TC now?  Anything?   If not, you might want to erase it and start backing up immediately, so you have at least some protection until you get the external HD(s).   See To erase everything on the TC's internal disk in #Q5 of Using Time Machine with a Time Capsule.
Then see #Q1 there for setup instructions.  If there's a problem, post back with details, or check Time Machine - Troubleshooting.
Also don't hesitate to post back if this isn't clear, or you still have questions.