Sid,
You're welcome regarding my skinning toolbox.
I wouldn't really say that I prefer the HTML to .ascx skinning, I use both where they're quickese and seeing as I'm an HTML and CSS designer first, this is what I'm most comfortable working with. That said though there are some very good reasons I work with HTML first, before I convert a design to DNN:
The output of any DNN site is HTML, if you look at the source code it's all div's and CSS, and having tried to work directly from .psd files straight to DNN skins it always took me much longer and the skins were confusing to put together. By starting at the end, and creating nice clean, semantic and valid code, it's then just a case of removing the to-be-dynamic content such as navigation, contentpanes, user links and stuff, and replacing these with DNN skin tokens. It also means I've already gone through the hassle of styling most of the skin tokens and the navigation within the skin.css file and because we can render the NAV as a UL now, there's less work than if I'd went straight to DNN.
I do work with the .ascx file after I've created the initial skin and installed it. The skin.xml file and HTML files are only needed by DNN to create the .ascx file, so once it's done the hard work and converted it to .ascx, I'm comfortable to tweak this as needed. It also means I don't have to repackage the skin files and upload them every time I want to make a change to the layout.
After many years of working with DNN, this is just the way that I've fallen into skin development, I used to work on a hosted site, skinning directly into DNN and my technique has developed as I've worked with other CMS platforms like Joomla and WordPress. I've found that at first skinning for DNN can be quite daunting because a lot of the resources are slightly out of date, like the skinning guide, and there's not a lot of "this is easy to do" approach taken with skinning. At the end of the day a DNN website is really just a system for creating HTML content, and creating skins isn't that much more difficult than creating an HTML layout, so I suppose that's why I work predominantly in HTML over .ascx.
I know that was kind of a long answer, but I think it answers your question :)
Rick.