I am sorry you misunderstood the purpose of the installer or DNN for that matter. And IMHO that's what happened here. Why did you assume that running the installer on your machine would allow you to install software on a remote server??? That is rarely (if ever) done due to complications with the Internet protocols, security access rights, etc. The purpose of the Installer for a "local" installation is because for you to install it on a server you have to run it there, at the server console, or remotely via Terminal Server.
In addition, let's be realistic, DNN, as the sophisticated Web application it is, is a complex beast. That is why the Installation package came to be. But I am also afraid that the Installation package creates the illusion that DNN is an "end user" type of super easy solution to create neat Web sites, like when you buy the Microsoft Office package and insert the CD. I can install DNN 4.4.1 on my PC or my server in a few steps but I have done this many times and I know that my machines already have all the required components installed, configured, and working properly, these include IIS, SQL Server, and ASP.Net. A good understanding of how these components work make the installation of DNN much easier, even for first timers.
There is nothing wrong with the direction DNN is going, like I said before, it is a sophisticated AND complex piece of software. I don't think that any Web application will ever be capable of developing an installation process for end users because they can try to install everything properly but when something goes wrong, like in your case, all hell breaks loose and the end user does not know where to start to diagnose the problems. You don't mention who your hosting company is but many hosters, and their support techs, support DNN with no problems. If the technician from your hoster gave you the opinion you quoted about DNN is because he is no good AT ALL with IIS, SQL Server, and ASP.Net, and that's all DNN is.
Again, sorry for your bad experience but maybe your expectations were not totally realistic. One more thing, the Installer is BETA software (clearly stated on the download page), shame on you if you didn't have a good backup before you started.
Please post any questions you may have before you attempt the installation again and the community will help you.
Carlos