I think the quiz is missing a couple of very important points:

• Size/Scope of DNN Sites: I could go deploy 100 tiny sites with default installations but would that make me a DNN master?  On the flipside, maybe I've deployed a company intranet with 1200 users, over 50k hits per week, and *the* source for all the information in the entire organization and this single site is what dominates the majority of my time.  -- for me personally, I've deployed just that, a massive company intranet with over 800 pages, thousands of documents, several custom modules, some purchased, and so critical that if it goes down for the 10 second app recycle when uploading new modules the phone rings off the hook.  Aside from my day-job I have deployed a smattering of other sites (< 10) but that would qualify me as a newb.
• Modules developed: Not talking about quantity but scope.  I've written a few commercial modules, a couple free ones, and then several "internal-only" modules.  The internal-only modules range in size from only a single class to over 30k lines of code + hundreds of lines of javascript and SQL queries/stored procs.  One such module I just released as a second beta at my day job and have spent the last 6 months working on it.  Your quiz doesn't even look at this as a possibility.
• Books written: Just for fun... seriously though, there are only a select few (Mitchel Sellers, Shaun Walker, etc) that have actually written a book.  But seriously... you write a book, you *must* be serious.

I realize the quiz is "just for fun" but it isn't really representative of the true capabilities of a person.  I don't consider myself a newb in any fashion, definitely not an average user, but I don't have over 50 modules, 50 sites, 10 skins, etc.  I have WRITTEN skin objects, several modules, and I've been using DNN since the very first 4.x release.

Just my two bits, rehashed.

I've added additional questions and a new score range definition based on your feedback.  Check it out and let me know what you think.   Perhaps you have your own questions that you think might be a good addition?

Chris, correct answer for upgrades from any DotNetNuke version >= 4.6.2 is: No, you don't need to touch web.config, the upgrade process will take care of it using XmlMerge.