Hi Mike,
Yes - it is pretty good fun living on a boat.
For the "basic product" of MultiBit i.e. what people use to send and receive bitcoin I am quite happy to help code it all up and get it out there as we are doing now. Hopefully by the middle of 2013 we will have:
+ encrypted wallets
+ Bloom filters
+ HD wallets
+ Trezor support
+ fee calc support
At that point I think MultiBit/ bitcoinj will be 'done' (don't laugh please!). Then all the interesting stuff that is possible with Bitcoin but is not being worked on deserves re-looking at.
That could be assurance contract driven definitely. It depends a bit I think on what licencing the people putting up the money ask for.
At this point in Bitcoin's life there is still a big chunk of infrastructure work that needs doing. Keeping that all open source I think is preferable.
I don't think we are going to run out of things to do.