number 2 if you have lots of dvds or even a few get a video converter program... i use cucu soft dvd to ipod converter it costs about 30$ via download you can google it. you just put your dvd in click a couple of buttons and it takes about 30 min for 1 hour of video to be converted for use on your ipod. So long as you own the dvd of the movie this is not illegal in any way. this is by far the cheapest way of getting videos on an ipod.
A word of advice, the "not illegal in any way" may be a bit of a stretch, but many consider it fair use. The problem is that there are anti-piracy encryptions that by circumventing those, that portion is the grey area.
However, if you are looking to take DVDs and put them on your iPod, I suggest
Handbrake. It is free, and works great. There is an iPhone/iPod touch setting, and and episode of an hour long TV show (so about 45 minutes of video) takes up about 250 MB using the iPhone/iPod touch preset.
You will also need to have the free
VLC player installed as well.
Both work on Mac and Windows.
As for how long, that
greatly depends on your machine. On my iMac 2.66 GHz Intel Core 2 Duo, with 2 GB RAM, using the 64 bit version of Handbrake, and nothing else going on at the time of encoding, I get about 90 Frames/second, which is about 3 to 1 (meaning 45 minutes of video is encoded in 15 minutes). Your results will vary. My older machine? A 2 hour movie would take all night (starting when I went to bed, generally done when I woke up).
The easiest way (that won't help your existing movies) is to start looking for the versions with a Digital Copy. For instance, most Disney releases recently, there are $10 off coupons for the bluray, and these many times include the Bluray version, DVD version, and a digital copy.