Somewhere down the line you're going to sink many $K into marketing, I don't see why paying for a domain name that already has some traffic and name recognition is a categorically bad idea.

Was it a bad deal for 'freedrive.com'? Depends on the specifics of the situation and how the company leverages their name recognition.

Depends on a lot of factors, but your pagerank can be a huge deal for many sites still. People deep searching into your content, when they didn't even know they were looking for you, is huge ... if that applies to you anyway.