OK this is what I did, totally depends on one's preferences but I bet you can figure it out.
First I created two smart playlists of the stuff I want in the player, Both in one folder named "Sansa" so I don't forget. Both playlists are limited in size, and they add up to 1.75 Gb, my player is a 2Gb, leaving some wiggle room for Rockbox.
First playlist is limited to 0.875 Gb and is made of Any song rated over 2 or that is unrated, sorted by added date. This gives me the most recent songs, exept for the ones I dont really like that much.
The other one has the same data limit and is sorted by rating, giving me all the five star songs and if there's room some fours or even threes. I only wish I could shuffle this one as it only brings up the same list of songs. Maybe a list limited by size AND rating in random order? I'm afraid this would bring up too many four star songs.... ah the dilemma!
Anyway, I just drag that folder into an empty folder in the player and all the songs are copied. Pretty neat huh?
Any comments on this? Suggestions?