iOS device playlists - best practices

So here's my conundrum. I have many playlists in iTunes, for listening at home. I want to sync the "best of" each playlist into my iPhone, but still have the songs organized in the same playlist names. For example, if I'm out and about and want to listen to a shuffled playlist of say, rock or mellow or whatever. I have yet to find a satisfactory solution.

I read about the checkbox field, which will only sync checked items. That sounded like just what I needed, however it has an unfortunate side effect of excluding all unchecked items even from at-home listening, unless I check them all again. But if I check them all again, that essentially ruins my iPhone library the next time I sync.

I could just do a smart playlist to sync anything I rate say, 4 or 5 stars...but then the songs don't show up in the right playlists, they all show up in the one playlist.

My current inelegant workaround is basically to have two sets of playlists in iTunes: the original playlists for at home listening which has everything, and pared down versions of all those same playlists for the iPhone (so for example I have Classical, and iPhone Classical, Rock and iPhone Rock, etc). This clutters up my playlist pane quite a bit, and it just seems suboptimal.

Am I missing a feature that might already exist in iTunes that would serve my purpose better? I know about iTunes Match, but isn't quite what I had in mind (plus that's more money). Any other ideas?

Thanks!