1. I had 17437 songs when I tested my media player against the TSU9600 (I have an escient emulation I wrote). This is a limitation of the curent implementaion. I will forward a link to this post to the Pronto Team as well but I make no promises when/if it might be supported.
2. You could add a 2nd device and have one of the Escient Hard Buttons jump to a page in that device. There is no way to add a page to the existing device.
3. My thoughts are that you would use Playlists functionality on the Escient. I own a DVDM-100 and there's no "Record" button to add to a playlist in the Escient device. This issue was also raised later in the 9600 Beta test. I don't know of a way to do this at this time.