What are the checks for next to the music tracks? In iTunes (puke) it
means to sync or not sync that file. But I don't see what they do on
gtkpod? I did see them listed as an option in smart playlists.

I'd like to know that too :-)

With iTunes I had to delete
it from the iTunes DB, sync to the iPod, then add it to the DB, then
sync again. Since gtkpod doesn't really "sync", is there an easy way
to handle this? Or do I really have to remove it from the library,
remove it from the ipod, then re-add it?
Nooo! You just edit the tags you like, on the tracks you choose. You can select a number of tracks and edit their common details such as album, genre... At the end you click on "Sync" or "Save changes" and that's all.
I notice gtkpod is really clunky performance wise when scrolling my
ipod's list of songs, or loading my library's list. Other music apps
perform much better at these things, but they are all semi-braindead
about the ipod itself. Switching from my ipod to my library takes
about 5 seconds, during which time there is no visual feedback. I
don't actually know if my click on "Music Library" actually registered
or not until those 5 seconds are up and it re-draws.

That's true, sometimes it's a bit slow
It would be really nice if gtkpod issued a warning when I am copying
too much data for my ipod.
Well I have all my music imported into my local music library. When I select a bunch of tracks to drag and drop on my iPod, I can see the amount of Mb below at the status bar

Once I have clicked on a filter tab, how do I un-click it? I am no
longer able to sort by my music columns! I get a Gtk-CRITICAL error.
Closing and re-opening gtkpod fixes the problem.

You unclick the filter tags clicking on "ALL". I don't know about the critical error... but I'd try changing the sorting options.
What I really would like is a playlist-like thing that I can
add/remove songs to at will, which is my ipod's "sync list". That way
I could manage my ipod without it being plugged in (it lives in my
car) and then just plug it in and sync. That way, if I overflow the
ipod, it's OK - I just get a warning that this sync list is bigger
than the target device. That way it would handle adding and removing
of files, I could have multiple device sync lists (one for my 80G
ipod, one for my 16G android phone, etc).

You can create such list as a smart list, and limit it to 80G. And then sync it exactly as you say.


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