Very sorry for the delay in getting back. My thoughts on engagement below:
DETAILS
* The docs I have read so far aren't actually structured to get public comment. They are a (long) report on what the group has done. So, fundamentally...
* What do you want people to comment on?
Do you want them to say: good luck, keep trucking.
Do you want them to give approval on the approach?
Do you want them to give approval of the broad plan?
Do you want comments on specific ideas?
Do you want people to say if they are opposed or in favor of specific aspects?
Do you want people to ask for more information on specific aspects?
You need to agree on exactly what kind of feedback you want. Otherwise you will get very little useful comment.
I would argue strongly that you need to create an entirely new document that is structured entirely around asking a few key questions. The main report can then be provided as a reference.
The report should have graphics, highlights, nothing at all about process and clear point for feedback including - importantly at this stage - the ability to ask questions that this group them provides specific answers to later on.
OUTREACH ITSELF
I would say there are three main groups of people that you need input from. I would recommend coming up with a strategy for each.
1. Others in the transition process but not following this aspect or caught up in one particular aspect and looking for the bigger picture. As things stand, this is the group that is being most catered to. It is also the easiest group to cater for. But, as a result, it is not the group that you should be spending the bulk of your efforts chasing - they will come anyway.
2. The broader internet community. That means all the people that are interested but have given up trying to follow the process. It means people that go to ICANN meetings. And it means the IETF etc. At the moment, this group is poorly catered for. You might get a small number of people tuning in who are interested but have not been following the transition process closely. But as things stand, their eyes are going to rapidly glaze over.
There needs to be much clearer and simpler communication around what is being proposed, and what the group wants feedback on. Any and all descriptions about the process or the amount of work done, and so on have to be ditched. This group does not care and will not care. But they do care about the end result and they will want to be informed and then heard.
3. Washington DC. This is a vital group to inform, whether you like it or not. Without the accountability work, this whole thing could fall apart. Plus, if Washington is kept informed and its concerns are listened to, it would also be a vital ally in actually getting the proposals introduced. If Congress says something has to happen for transition, the DoC will take that on board and ICANN will just have to get over itself and do it.
My recommendation for outreach to DC would be to ask the people in this process that are well versed in how Washington works to take the broad goals of public comments and the report and come up with their own materials and strategy. Then come back to the group for approval.
If it were me, I would approach: the IP folk - who are extremely adept at talking to Congress and have all the necessary contacts; Steve Del Bianco, who is known and respected in DC in this field; and Phillip Corwin who also knows his way around.
Unfortunately I would suggest not including ICANN staff because of the difficult relationship they have in DC and their inability not to meddle, although it would smart and wise and maybe even useful to keep the staff involved in open and honest communication.
If you wish to get some press attention - which is often a very effective way to be heard in DC (The Hill, Politico, maybe Washington Post) - then I would recommend Brad White of ICANN in DC. He knows all the outlets and the reporters trust him in a way they do not trust ICANN's other staff.
A few very concise, very focused briefings on the hill (they also will not care in the slightest about the process only the proposed outcomes), some credible people talking - Mathieu for example, Del Bianco, maybe Keith Drazek - some follow-up, and this group in particular could be in a position to turn around the whole DC conversation.
So that's my advice for what it's worth. I hope it's not coming too late to be useful.
Kieren