Steve,
We also keep a LOT (way over 100) of videos on a small hard drive. We recently bought a small Seagate HD that has WiFi and battery built in so we do not need any wires to watch video off of it.
I use 2 main programs to get video to the HD, BOTH ARE FREE!!
The first is "DVD Decrypter". I use it to make DVD backup copies on a large home hard drive. It puts out an ISO file that can be run back to a recordable DVD if the original is damaged or lost.
Next, for getting a copy of the movie or episodes of the TV series I recorded from TV or from that ISO file I created above, I use a program called "Handbrake". basically, you point this program at the ISO file of DVD (or to a DVD) and then tell it what type of output file to make. I normally have it make an MP4 file and drop it on that WiFi hard drive.
The files I keep on the small WiFi HD are NOT high deff, BUT for a small screen (up to about 10 inches) they are just fine! For our small LED projector for 25 to 60 inches I go direct from a DVD.
Greg