I am currently looking at how a user interacts with their timeline, and this is a problem I have considered as well. The problem is that retweets are not always a result of a tweet appearing on a user's timeline. The user could frequently retweet tweets found in the public stream, trending topics, or the "explore" tab.
I think it is possible that your approach could work, but you would need to apply some filters to the kinds of users you look at. You would have to limit the amount of followers you look at, as many retweets come from very popular users. Crawling 10,000 users simply to track one retweet isn't really an option considering the limits of the API.
A more viable option may be to track a retweet from some user that retweeted it. For example, say you have User A, who retweeted a tweet that originated from User B. You can look at all of the users that User A follows, find any candidates that have retweeted User B's tweet (including User B itself), and then search the users they follow, etc, until you reach User B. It would resemble a depth-first-search (or breadth-first, depending on the implementation details). However, you could run into a problem if any retweeting user along the search is private. In this case, you will not see their information and the path of retweets is broken.
I know this isn't a black-and-white answer, but hopefully this helps a little. It's an interesting question.