I also believe if I expect to get my playlists RockBox, I'd still need to use the "search&replace" for that too. I might just load all my songs into the thing and just use it as a big "Recently Added" playlst.
I'll check out those options on iTunes as well. I appreciate the help.
EDIT: Tested it in iTunes out with a small playlist and definitely worked using the "search&replace".
If I get new songs via my phone then add it over to the music folder on my PC that contains all my songs, will that auto update my iTunes library or will I need to manually add it to my iTunes library?
EDIT 2: Just tested it out. Yes, they are auto added... nice... that does make things a bit easier.