Hey Wes:
I can certainly understand your perspective. In my day job (at DNN Corp), I deal with on-boarding people new to DNN on a daily basis. Therefore, I can tell you that DNN Corp and the entire DNN community really do care about new DNN users. Go to any community event, and this is certainly the case.
The problem with installing DNN is not DNN at all. As you mentioned, nearly every issue experienced with DNN (regardless of route chosen) has to do with the system it's being installed on. These issues always relate to how SQL Server, IIS, of Windows itself is configured. (These very few dependencies are a testament to everyone in the community that has contributed to DNN over the years, as projects that do similar things require so much more in order to function.)
Those of us who have been around for any length of time first fell in love with DNN due to the ease of installation in comparison to other web applications... Download to a folder, extract files, set permissions, create database (if necessary), add a site in IIS, view the site. Done. The rest of the "installation" of DNN is done via code - for you. However, all of these things require that you have at least a basic understanding of how the web works. You needed to be technical. This is the only way DNN "installation" was presented to new users a few years ago... We changed that.
In the past, you need to know what a database server is and how to install it. You need to know how to install and configure IIS. You need to know where to find the .Net framework and how to install it. You need to know how to apply permissions. These are all very technical tasks and require installation of other software. For these reasons, an installer would seem like a great option, but you might imagine how complicated of a tasks it might be to even plan to build a desktop installer that would successfully install DNN under every possible configuration of IIS, SQL Server, and Windows - much less the instances where IIS, SQL Server, or .Net are not presently installed.
Microsoft builds the ones you mentioned, Web Platform Installer (WPI) and Web Matrix. They (Microsoft) write every single line of code for all of the dependencies of DNN, and even they couldn't get it right. This alone should tell you how complicated of a task this is. That being said, we interface with Microsoft regularly when we find a scenario that doesn't work. If you've ever used WPI in the past, you might recall that it pretty much never worked. The unsuccessful installations I still see today relate to one or more of the dependencies already been installed and configured. WPI has numerous instances where it either can't or won't change your configuration settings, and for good reason. Who knows what would break if that were to happen...
If anyone ever has an error with WPI installing DNN, copy the WPI error from its log and create a thread in the forums. We'll forward it on to Microsoft for you to make sure that a fix makes it into a WPI update. You can find the log in the following path on your computer. Just make sure that the last app you attempted to install is indeed DNN.
%localappdata%\microsoft\web platform installer\logs\webpi
As far as the latest version of DNN being integrated into WPI and Web Matrix... We have a long list of tasks that constitute officially releasing a new version of DNN. So many tasks that there're more than one person involved and it literally takes an entire work day. One of these tasks is to forward our latest install packages to Microsoft. Once we do that, the only thing we can do is check on the progress, but you can expect for the update to happen in no less than 5 work days. I don't have an update for you as to why they haven't updated the latest release is such a long time, but I already have asked for an update internally.
If you want to have a quick way to install DNN, a community member out of Orlando has created a fantastic installation tool, but it does still require that you have the right versions of IIS and SQL Server already installed and pre-configure. Still requires a technical person to be involved at some point. (Also, I would only recommend using it in non-production environments.)
Hopefully, I've given you a little insight into some of the challenges, but I really want to let you know that we do indeed care. We don't only care about any individual edition of DNN, but all editions. Without DNN Platform, no one would ever discover the Evoq solutions - and without the Evoq solutions, there wouldn't be financing for an engineering and product department to ensure that there are monthly releases, QA, website engineers, and so on. DNN has never in history been released more consistently and with more stable releases than any other point in history.
I've been around DNN a very long time now... I know and love DNN more than most. I deeply feel and have to balance the decisions of community and commerce on a daily basis. Every decision myself and others make will always benefit one or the other more, regardless to the decision made. Someone will always feel like they're favored or not. This is not easy and I am not making excuses - but we are listening. We see the forum posts, the blogs, blog comments, the tweets, and more. We are very sensitive to your concerns. We appreciate your feedback and we care about your success with DNN and the future success of those that haven't even found DNN yet.
I said all of that to say this...
DNN is at its foundation and always will be an open source project. I really miss the days where we all contributed. We stood together, side-by-side to do something to make a difference. When one of us saw something that needed attention, we did it. If we didn't know how, we found someone else in the community to help us, and we did it together. If it required access that we didn't have, we asked to help someone that had access. If we discovered new information, we blogged about it. If we didn't know something about DNN, we asked. We shared all of this with each other on the forums, in user groups, and in social media. That's how all of the community leaders and MVP's have gotten to where they are today. That's how DNN has grown to what it is. That's how you ended up here.
This kind of open source participation has built thousands of lasting relationships and businesses over the years, resulting in our beloved DNN community and ecosystem. It is this ethic, passion, and level of caring and involvement which sucked me in to DNN in the first place. Please help me and the rest of the community continue this tradition...
You can be a community leader too... Participate.