Great post, cheers!
I'm a huge fan of Rachel's, she has and does give a lot back to the community, not to mention that Perch is a superb CMS, and well worth the money.
It's a sad thing to hear that someone who is responsible for a successful tool, as well as the contributor to many a conference, doesn't own her own home, or have a pension. Being a freelancer is many people's dream, but there is clearly a scarier side.
Useful post. Saving and contributing to retirement plans is very important for freelancers to do if they're able. Also, in the US it lowers someone's tax burden as well.
It is also interesting to consider the pros and cons of putting oneself out into the world (in the form of a side project or speaking engagements) versus solely focusing on paid work. It is a difficult to find the right balance.
"When experience can work alongside fresh ideas, I believe that is where some of the best things happen."