Hey man, thanks for the reply. It's good to know that it sounds like there is a solution.
Right off the bat, I don't think syncing certain playlists will work. There are many playlists I have that I want on my phone but I don't necessarily want all of the songs within that playlist to show up. With the way you described it, I could get all of the songs I want on my phone, but also get a lot of ones that I don't want.
For the auto playlist thing, is there a page on the wiki explaining that? It sounds like it could work. My question to that is if I try syncing other playlists to my phone, will it sync the entire playlist or just the checked songs? And will this autoplaylist have to be visible on my phone (it's not a big deal if I have one extra playlist on my phone that I don't need as long as it solves my issue).
Thanks in advance!