I don't use the remote much either because I tend to just listen to entire albums at a time and I have a play list for each album so I just need to select that playlist.

if you want a flatter play list structure why not just make one you can organize the songs and play lists any way you want.

the features you are asking about are not documented because they have only just become avaliable in the beta version of the 2.0 software. I am sure there will be some kind of manual made when the final version of 2.0 comes out. the book with the player is for an older software version.

insert/ append modes are selected using the select mode button on the remote when searching and can be selected by pressing in and holding the knob while browsing the playlists. insert just inserts the selected song next in the play list you are currently playing append places the selected song at the end.

bookmarks are used to save the current position and playlist of the playlist you are currently playing. so for instance if you are playing all the songs on the player in random order then you decide you want to play a particular list you can save the one you were playing and go back to it later.

keep posting on here it you have questions or problems someone will probably be able to resolve them.