Running Out of Space... Help!

The hard drive on my 250 GB Macbook is almost full (I have 1 GB left).  My 500 GB external hard drive is almost full (I have 23 GB left and it requires 27 GB to do the daily back-up).  Without buying a new laptop with a bigger hard drive and without buying a larger external hard drive, what can I do?  One thought-- I could clear my external hard drive and then do a complete Time Machine back-up from my laptop to the external hard drive, which should take up only 250 GB of the 500GB external hard drive.  After that, I could then delete from my laptop hard drive about 80 GB of movies (many of which reside in iPhoto).  Does that strategy/sequence make sense?  Are there any dangers to this other than a power failure while I am doing the transfer from the laptop to the external hard drive?
If the above strategy/sequence makes sense...
(1)How do I delete what is currently on the external hard drive (without having to re-format it)?
(2)How do I quickly find all of the movie files in iPhoto that I will want to delete from my laptop hard drive after they are backed up on the external hard drive?  Is there a way to do this short of going through each album and deleting the videos one-by-one?
(3)In the future, if I want to access some of the videos that reside only on the external hard disk, how do I search for them... will they stay in the albums from iPhoto?  How do I open them from the external hard drive?
Thanks in advance for any time/help/suggestions you can offer on this...

Freeing Up Space on The Hard Drive
  1. See Lion/Mountain Lion/Mavericks' Storage Display.
  2. You can remove data from your Home folder except for the /Home/Library/ folder.
  3. Visit The XLab FAQs and read the FAQ on freeing up space on your hard drive.
  4. Also see Freeing space on your Mac OS X startup disk.
  5. See Where did my Disk Space go?.
  6. See The Storage Display.
You must Empty the Trash in order to recover the space they occupied on the hard drive.
You should consider replacing the drive with a larger one. Check out OWC for drives, tutorials, and toolkits.
Try using OmniDiskSweeper 1.8 or GrandPerspective to search your drive for large files and where they are located.

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