Re: qn #1 ... Do you believe in the concept of UI auto-generation from metadata? ... I'm definitely going to answer 'yes' to your first question, being one of the committers to the Naked Objects (Java) framework and writing a book on DDD + NO.
The question mentions metadata. I think this is key to NO being able to succeed. In the latest version (which will be going beta in Feb) the metamodel has been opened up so that it is very extensible, either so you can write your domain model following your own programming conventions/annotations, or, potentially so that more sophisticated viewers can look for their own metadata to provide more sophisticated views. (For example, consider that if an object implemented a Location interface then it is displayed in a google maps).
Regarding qn #2 ... what kind of problems can be approached this way ... we've always said that NO is more suitable for "sovereign applications" (transactional, operational systems ones used internally within an organization) to "transient applications" (like an airport kiosk, say). An NO GUI does require that the user is familiar with the domain, otherwise they won't know what they are looking at.
What's missing still is sophisticated viewers, of course. You are right about the NO GUI, it is definitely low fidelity (though the .NET version is a big improvement, see recent infoq.com article). On the Java side there is a sister project called scimpi.org that has a lot of promise though... it provides a basic web GUI for free but lets you hand-craft web pages as necessary and incrementally. I'm also working on an Eclipse RCP GUI that'll work similarly.
The other thing to add to this though is that the NO approach has value (I believe) even if you choose to write a custom GUI and/or presentation layer. That is, you can use it as a design tool for building a very solid pojo domain layer, and then skin it as you will. Trouble is that NO was never originally sold in those terms, so most will see the NO pattern as an all-or-nothing affair.
Dan