Questions about movies in iTunes

I like our new iPhone and still need the iPod Classic because of its nice large hard drive (which still doesn't hold all podcasts).

I bought the Classic more for its ability to share pictures than to play music.

Photo Stream's nice, but not for > 1,000 pictures... which for us is not for > 3-4 months ago.

So having all pictures on the Classic helps us share with Mom and others, via the Classic, and better... via the TV screen (via the cables).

To do this, I have, every few weeks, dragged and dropped the home camera movies from iPhoto into iTunes.

When that happens, only the name comes across, no date information.

So, to then have the movies in a good sort order (since we had more than one camera, sorting by file name doesn't work), I needed to manually name each one.

Questions:

1) How to get all deails about the movies, especially the date/time stamps, from iPhoto into iTunes?

2) If we can't do that... is there a way to use automator to, after I highlight a movie or group of movies and press the macro keystrokes (does it support that??), read the number of the current highest-number movie (I rename to Video###) + 1?

With either of these, my life would be easier getting all content onto the iPod Classic.

On a related note...

Some podcasts don't download in a format that works on the iPod.

Is there a way, beyond the manual one I use, to convert the file formats automatically to the one that plays on iPods?

Thanks,

Mike