In my opinion, starting at the beginning of a playlist is the last place one wants to start playback.
The most desirable starting point is the last track played and continue from there. This makes a natural flow to play the entire collection (investment).
We have talked about this several times, but never got off the ground.
May I suggest for each smartlist/playlist an option when selecting that list to search down the tag fields of "last played date" for the most recent date, in meta data this is a simple integer. Look for the "MAX" value and start play back from there.
You will make many, many music users very happy by doing this.
Regards, Harrun