I went through some contortions installing 4.4.1. While removing the "Comments" from the Web.Config is something any ASP developer would notice mgrimaldi does make some points. When it comes to the connection string/database this is not a fault of DNN. I put the software on two different web servers (DiscountASP.Net & Gate.com) as well as a local installation for development. All installations use IIS, ASP.NET 2.0 and SQL Server 2005 (note not the Express Edition). All three installations required differing connection strings.
Local installations was a bit more troublesome as the "installer module" created by someone did'nt work for beans. I had to manually set up SQL 2005, IIs and Visual Studio 2005.
As to "comments" in the files that are DNN I agree. That is to say the Source Code is sparse as far as comments go as are the module sources. Documenting Source Code is Programming 101, one of the first things taught in computer science. It sure does make things difficult for developing and understanding how DNN works.
With that said, DNN is a fine piece of work and the coding in the core framework is excellent.
As to your task itself mgrimaldi do realize that DNN is a framework, it is not a Content Management System (CMS). Joomla or Mambo are excellent CMS systems and performance/functionality wise will run rings around DNN. However, they are not portal frameworks.
Many people seem to confuse this distinction. The popular CMS systems like say Joomla have modules/Mambots/Components that will pretty much do anything one can do with a DNN portal. But, they are not portals. Thats an important distinction. DNN can create multiple sites from one installation and through that be efficient in doing so. Mambo, Joomla etc. are singular installations.