Sure. Here's what I do (and I have a LOT of TV shows... 30 GBs or so).
I rip the episodes from the discs and name them like this:
"
season.episode episode name.mp4".
So the first episode of
My Name is Earl would be "
1.1 Pilot.mp4". (I don't really care how iTunes sorts stuff but if you do, you might want to drop the name of the series in there like "Earl 1.1 pilot.mp4".)
Now, when I drop them into iTunes they sort by title. 1.1, 1.2, 1.3, 1.4 and so on. Of course anything you add to iTunes goes under "movies" as you probably noticed so you have to get info on the show and change the video type to "TV Show". Also change the season and the episode number here.
If you have a lot to change, doing it one by one will suck, so
go get this script. It will batch change the video type for you on as many episodes as you select.
Now, my shows appear under "TV Shows" in iTunes. Now I just go over real quick and clean up the names. I take out the 1.1, 1.2, 1.3 parts of the episode titles and put that info in the "Episode ID" field instead. You don't really need this, because if you fill in the "Episode Number" field, then sort by show, it will line up in order (I do it anyway because I keep thinking it may come in handy one day and I like to view it in iTunes sometimes, but for some reason "episode number" is not a field you can view in iTunes' columns -but "episode ID" is).
Then I add a screencap of the opening title (instead of the default poster frame iTunes assigns) so I can easily see whats what in cover flow.
Here's my library on my PowerBook (not my main library, just where I do a lot of my initial ripping while I'm at the office).
Viewing by show:
THEN, just because I am finicky like this,
I go over to TV.com and copy & paste the original air date & episode summary for each episode into the long description field. How do I get into that hidden field you ask?
Run this script.
As for getting them on your iPhone I don't know if I can help. I'm an iPod user myself. But, once you have your shows all set up right in iTunes it should be a breeze.
Usually I use playlists for TV shows. If I'm re-watching a series all the way through (like I am right now with Arrested Development) I simply make a playlist, then load that playlist onto iPod.
I have a smart playlist that's kinda like my own TV channel. It randomly picks 12 episodes from any TV series rated between 4 and 5 stars (to weed out non-TV show material I have in my TV Shows section because it won't fit anywhere else) with a playcount less than 1. When I've watched a show it drops off my playlist (because the playcount is now "1") and when I sync it automatically refreshes the playlist to new episodes. I never know what's coming, it's just kinda like zoning out in front of TBS on a rainy sunday afternoon or something.
