I made the switch to Drupal without knowing much about the Drupal core blogging module and as it turns out, Drupal's core blog implementation is excellent, but was intended for multiple bloggers. This way a user could view the site blog page and see recent posts from any member, but could still view just the posts from a specific user (e.g. Taylor's Blog). This was good and all, but it bothered me to hack my URLs to fit my single blog site.
I googled my problem and there were quite a few solutions out there. I checked out the top two and these solutions were OK, but I saw a snarky comment on one of them saying just to use Story's with the Views CCK. I have only used Drupal on one previous occasion and used the Views CCK with a lot of success.
I decided to download the Views CCK, which lets you use a graphical interface to filter through the CMS data and display it in a customized fashion. Following the comments' lead, my idea was to make a "view" that simply displayed all the Story's (one of the default Drupal content types) in an blog-like fashion.
I added a few test story's and then went to the views interface. I told it to display only content of type "Story", to display a teaser, add a pager, limit five per page and sort it by date. Voila, it works perfectly. On top of that, I could easily make an account for my a friend to make posts and it would work like the core blog module. In addition, I could make some new views that displayed the content for each user to create the effect of individual blogs.