Earlier quoted context omitted.
Yes, a few months ago, it was ridiculously easy. It literally took me 20 minutes to customize how the side bar was working and embed some new dynamic content. I even inherited off a parent theme so any updates to the theme wouldn't over-ride my changes. I've never even written much PHP in the past. I even added it into the the theme editor so the client could change the text/etc. themselves. Not sure what you did, bu…
That's one problem with Wordpress' default renders; it sends developers down those relatively narrow paths of customizing existing output. It's easy if requirements are flexible enough to allow that, but not the right CMS for truly customized content architecture and presentation.
Can you give an example of something like that which is not possible with WordPress?