Userland speculation
While searching for answers to this post, I found a recent plea in the Manila discussion forum. Here's a response, posted here so I don't lose it.
Disclaimer: I'm not unhappy. I'm thinking outloud.
Almost all of the management staff have weblogs, but few are updated on a regular basis. Scott Shuda and Scott Young regularly update, but not about Userland stuff. The primary sites have been updated with extra documentation and links are better organized than they were even 6 months ago.
I think that you are correct with your basic assertions: as users, we need software improvements. In addition, we need some basic company stability, so I'm glad to give them a little rope to see if they can figure things out. I would estimate it will be the 3rd quarter of this year before we hear anything definitive. Take a moment and look at it from a different perspective:
There are two main products (Manila and Radio) that run from a nearly identical code base. When you change one (Manila) you run a risk of "breaking" the other (Radio) unless you understand them fully (only Dave does). Both products are actually too similar--you can do several things with Radio if you know the code. Hence, one of the biggest strengths and weaknesses of the Userland product base: the code.
The code uses a lanuage that is not currently in vogue, popular, or "generally accepted" as a standard. That is a weakness--developers code with what they know. Developers are key to a platform (ask Apple)--no developers, no apps. Radio and Manila developers could produce some great products, but the base is pretty small (again, ask Apple)--so it's better to spend their time and efforts on other things.
The code uses a lanuage that is not currently in vogue, popular, or "generally accepted" as a standard. That is a strength--viruses, bad hacks, etcetera don't show up on the platform because it's too hard for lazy virus writers to figure out. That means that we don't have a comment spam issue (see MovableType).
Since I'm just a user and amateur (really) developer, I can't complain: The code is completely open and mostly documented with "how" and "why" comments. If I want it better, I write a tool and ship the code. It can be used to patch the environment to make do what I want. I sell it and make money--Woohoo!
But, as an amateur developer, I also face the issues you mention: uncertain platform growth and new management team. What if I use the runtime to develop a theme-generator and try to sell it? Sounds great, but maybe that's the feature in "Radio 9" that they give away.
Take a look at TypePad, SixApart's web-based weblog service. It's snazzy, pretty, cool, etc. It's not that much different than Radio, but you don't get the source code for free and your content is trapped under something heavy, namely the SixApart server farm. Anyway...
TypePad is great and most everything I would want Radio to do. Whose to say that Userland isn't doing this right now? The infrastructure is already there, just the look needs retouching. Go all CSS making for easy theme generation. Write support for secure FTP to allow easier hosting off the Userland clound. Hell, for that matter, revamp the "cloud" by adding options for extra space, features and domain hosting.
Don't mistake my Radio emphasis. I'm using Manila on a test site or two, but the fundamentals are the same. Manila could use some extra polish (especially server management, site installation/deinstallation), but it's very usable.
Tired hands are forcing me to stop this rambling essay. Write your own in comments.