1) You can really only create 4 playlists. It is rather easy to do (navigate to the song using the wheel, hold GO until you get a menu that says "Add to favorites" and pick your color and let go), and easy to navigate (as there are only 4). IMHO, one of the main points of MOTS is that you don't *need* to create playlists - it creates them for you on the fly... you just pick the first song. I might suggest that one's feelings on this point separates those who like the BS5 and those who do not. If you really like to build playlists and need to listen to a specific song at a specific time or in a specific sequence, then the BS5 will leave you disappointed. On the other hand, if you'd rather not be bothered with building playlists and are flexible about how you get your music, then the BS5 is great.
2) If you're talking about iTunes on Apple, then you rip, add artwork, then drag and drop the songs from iTunes to BeoConnect (little app that lives in the dock). If you're talking about Windows, then you must use BeoPlayer to at least attach to the BM5 (map the BM5 to a network drive on your local PC). Then you can drag and drop the files using the file system, but I have no problem wiith BeoPlayer (insert CD, wait for it to find the track names and artwork, drag the album/songs to the BS5).
3) There's very little that you can do with the remote so I don't see any reason for spending extra money on the Beo5.
4) I believe the BM5 only works with B&O TVs.
I hope I haven't talked you out of it, but if you want very specific control vs. the BS5's automagic, then I'd recommend using an iPhone or iPod Touch with a remote app vs. BS5.
Stan