I started playing and blogging Wellington back in December 2008 so it can all look a bit overwhelming if you're a first time visitor.
You can start reading anywhere you want. I usually connect each household's updates with links to the next and last update so you can follow your favorite family through time. I also link to things that have happened in the past so you'll get an idea what incident I'm writing about. If you want to start on a specific round, you can find a tag in the sidebar for each round.
If you want to start reading from the beginning, this is the place to start. Everything before that is either a sim profile or an information post which is linked in the sidebar.
The sim profiles hold important information of each sim but may contain spoilers if you're reading from the start. I don't know a way to work around it so just consider yourself to have been warned.
Feel free to leave comments anywhere, even in the older posts. I love hearing readers' thoughts about my sims :)