Chris,
I'm not too surprised at the length of the document, since we have now turned it into an educational tool. Even beginning to communicate the intricacies of ICANN and IANA in a few pages is a challenge -- but we decided to make this "primer" a part of the document. (I'm not sure the questions are entirely "distinct", a number of them are related, but that is of no particular moment.)
In any event, my understanding is that a small group of members/participants in the CWG would select the lawyers, with some assistance from ICANN, and that ICANN will pay.
It's always been clear to me that we would need to engage a law firm, and not merely a single lawyer, to get the advice we need. Most lawyers of the calibre we need work in law firms, not as solo practitioners, and don't work in isolation in any event. It will be important to engage a lead counsel with the core skill sets we need, who will coordinate and provide the bulk of the advice, but would do that with the assistance of his/her colleagues.
Greg