hello just someone,
I never try AIFF on my iPod; these files are too large to be usefull on iPod. As said before, AIFF is an exact copy of the audio information of an audio CD. The best way to encode and compress these files is definitively AAC at 256kbps.
I'm not sure if you mean by "skipping songs" you mean that your iPod went to the next song passing over an entire song or you mean skipping a few seconds within a song. If its skipping within a song, it may be related to the fact the AIFF file are very large and that the buffer of the Ipod is getting full with only a too small time segment. A good way to verify this will be to convert a few song to see if it is solve the problem. keep in mind that an iPod haven't been designed to play AIFF file.
beside, converting your song isn't a lot of work. go in your iTunes preferences pane in the "Advanced" tab and then in the "Importing" sub-tab. Select AAC encoder ant the quality you setting you want. then, go back in your library and select all the song you want to convert. then click on the "Advanced" menu and select "Convert selection to AAC".
this will convert all your selected songs. they will now be duplicate but easy to manage by doing the following; right-click on any column title and select from the list "Kind". You will now see the audio file kind in your library window. You can click on the column title "Kind" to order all your songs by kind and this will easily allow you to delete duplicate format as you desire.
I hope this will help you, regards,