In my opinion CL is great for the traffic it can drive but not good for link equity.  I'm pretty sure they nofollow all of the links from Craigslist so the only real value is the traffic.  If the listings are expired and still cached by craigslist I would suggest seeing if you can't login to craiglist to manage the ads either by adding new ones or possibly deleting old ones.

I agree with both responses, there is no reason to 301 redirect just because of new title tags.  I think 3 redirects is really pushing it in terms of retaining your link value but 2 I have done several times with no effects on rankings.

Hope this helps!