What is going to happen to UserLand? Here is what I think will happen. Jake and Lawrence will continue to move forward until the paychecks stop coming, and perhaps a little further. Eventually it will be just Dave, yet again. This will have to be after he finishes his fellowship. If Jake and Lawrence go away before Dave completes his fellowship, the community will be on its own. Will the UserLand products go way? No. UserLand has a cult following.
Here's what I think should happen. This would be a perfect time for UserLand to open source its products -- including the binaries -- and set up a structure for code submissions, reviews, testing, and releases that the community can support. Jake and Lawrence could establish the foundation projects, manage the code base, and facilitate the release process. I believe that this would be like an adrenaline shot for UserLand. It might be time to truly put these products in the "User's Land."
I know I would feel a lot more comfortable investing more time and energy in Manila, RCS, and Radio if these products were being built and maintained by the community in structured projects or in the hands of a larger company.