Much has been said about Drupal vs WordPress in the past, see references at end of article.
This post is geared towards the end user and project manager that wants to select the best system for their needs.

I am going to talk about our direct experience only, so all following statemets have “In Our Humble Experience” preceding, please take that into account.

Also, drupal 7 has set out to improve usability in the default install, so this article will become irrelevant in several months time.

Ladies and germs, without further ado

Drupal vs WordPress – who wins?

1) Blogging – WordPress wins with a K.O.

WordPress is wonderful for a simple blogging solution. The user interface

Blogging and CMS are very much a gray area as far as people’s definitions go.
After all, WordPress allows for static page creation, comments, and user submitted content. Just like Drupal.

2) Ease of install and Administration – WordPress wins on points

Timewise, WordPress takes much less to install out-of-the box.
End-users find it easier to use.

However, advanced modifications take less time in Drupal. Drupal has allowed us an easier shopping cart integration with Ubercart and the multitude of Drupal modules is inspiring. If you were to create dynamic content with multiple fields (price,location, size, etc),

Drupal is Uncontested Winner in Heavy Content Supremacy

If you have the money to customize, Drupal is the way to go.

Resources
Gradual change article