I have installed DNN on my production machine twice over the past 2 years, bought books and subscribed to DNNCreative.  But everytime I get ready to commit to installing it to my site there are 3 things that stop me.

Categories - I see many article, and other, modules offer categories but see no way to manage site wide categories.  Similar issue with tagging but no sitewide categories is a real deal breaker.

Searching - There's no advanced search.  I've always offered many ways to search (category, type of content - article-blog-forum, author, date, exact/contains, etc) but haven't found any module or code hints on how to add this functionality.

Master pages - Clients just don't "get" creating a new page and having to add the same modules to left/right content as other pages on a site.  It's also a time waster for me.  I really, really need someway to setup a master page, or similar concept.

I really, really don't want to have to move to a PHP/mySQL solution, or fee based .net CMS, but that currently seems to be my only options.  I'm sure DNN is great for ENTERPRISES with multiple portal needs but it's really difficult to use fit the needs for SMB, single site clients.  Things like having all DNN css in the FCKEditor "Style" drop down instead of just referencing one CSS file for use by editors, separate portal/site admin, each page having to redefine left/right columns, types of navigation.

Categories

I've spent years in the eCommerce world so my expectations are that content s/b just like a product that can be assigned to multiple tiered categories.  It can be done in modules like DNNArticle but there's nothing sitewide where I could link page/tabs to multiple categories. What I'd find most useful w/b to apply view permissions by category and then ovverride, as necessary, at page and module level for an entire site.  Instead there are some modules that offer categories, even core modules like "Store" or "Help", but none of the modules share their category structure with the site, or other modules.

Search

There's no use in putting a bunch of content in a site if no one can find it, which makes searching a core function. Since search appears to be a version 1 core module, I'm guessing it's never been improved.   I've previously looked at Venexus and it appears to only add pagination and any/all searches.  Nothing for date, nothing to search by module or forum .  Venexus even recommends not searching forums.  I tried searching the Marketplace (which is more like the search I'd expect for DNN, including categories) for "Google Mini" and "Google" and didn't find anything.

Even on this forum I can't research any previous postings on something like "categories" w/o getting 35 pages of useless results.  First "page" of ten results is all about categories in Modules such as "Repository", "Online Help", "Feedback", etc.  They're all from 2007, except for one from 2006.

Master Pages

I'm getting better at skins but so far don't see much resemblance to master pages, except for being able to use a few tokens.  I don't see any way to have, for example, a DNNArticle categories always in the top position of the leftpane.  Yes I could have clients copy an existing page but then what if I want every page on the site to change to display DNNArticle categories in the second position on the rightpane?  Might as well go back to static pages w/o a template or include file.

Sorry I don't think any of these issues "work well".  I've seen too many other implementations in PHP, or even from ASP 10 years ago,  that handle site layout and content management far,far better.  From a setup/maintenance POV this feels a lot like the days of static HTML sites and licensing services like

Christie Mason
(still gritting my teeth that even though I have "notification" checkmarked, I still receive no notifications)