MGrimaldi:
I will try to help you as much as possible within my time constraints, just like everybody else in this forum, but that is only because I want to share my experience with others, not because you are giving me that designation. However, you need to post the details of your problems. So far you have not mentioned one of the specific errors, problems, or messages you are getting IN DETAIL. You can start by telling us what version of DNN you are installing.
I would also take your challenge to install DNN, any version, on any server or PC, with SQL 2000 or 2005, any time, and without the book and I can guarantee you without any doubt in my mind that you will see the portal running in under 30 minutes at the most.
Also, and I have said this before several times in this forum, the fact that there are many people asking about DNN installation issues also proofs that the product is extremely popular. For your argument to be valid you would have to see how many of those issues were impossible to resolve like you are saying yours are. You are going to find that not many. Also, few people post their success when the installation works the first time. I just made a second installation of 4.4.1 on my TabletPC for development and it worked the first time but I did not post it.
Take a step back and realize that DNN, even with all its internal complexity, is nothing more than another ASP.Net application. Also realize that DNN actually works (just trust me here), so there must be some fixable issue you are missing (no intention to offend or diminish your knowledge, it just happens). Off the bat you mentioned that you have separate IIS and SQL servers, that configuration introduces issues related to the connectivity to SQL that you need to address, based on your experience, you should already know how to set this up and test it outside of DNN. Also, when you get a page not found error, it may be related to the fact that on the server you may have already be running another site on the default Web site (maybe Sharepoint), but hopefully you already know that you need to create another site with a corresponding Host Header to avoid that issue and are not trying to run from localhost. There are also issues with ASP.Net 2.0 and separately with SQL Server 2005 that many users and developers, not necessarily exclusive to DNN, need to address, but you are probably familiar with these too.
Regarding DNN as freeware, that is indeed true, but also notice that there is now a formal corporation backing DNN and it has close ties and the cooperation of Microsoft itself. If you work with Microsoft based solutions, I challenge you to write a Web based application as solid, secure, and expandable as the DNN framework.
And one more thing, something you will notice if you take a breath and calm down a little bit, is that this community is not composed of geeks with no life. One thing that I always say separates this community from other technical sites is the maturity of its members. Actually only a few of the people here are hobbyists in my opinion, many use DNN for commercial and government sites, this also applies outside of the US.
Again, if you want help post the version of DNN you are trying to run, whether you can run other Web applications on the server (possibly based on ASP.Net 2.0), and whether you can connect to the DNN database on the SQL Server from the IIS server.
Carlos