Hi Synergy,
As a Mac user, I found dragging and dropping music to the Serenata in mass storage mode was simpler than using the iTunes plugin. It worked similar to getting music on an SD card for a BeoSound 2. You'll need to remember that album art isnt possible when using a Mac.
Battery life for the audio playing through the speaker, an hour or two if I remember (been a while since I used mine), but you could always use the docking station and have it charging whilst playing? Although depending on the duration of your appointments, it may last for a session and then be able to get charged between, I'm not sure.
I'll private message you Re: selling!
Robert.