I would go and check out each one in person, pull out each drawer, look at the rust spots. I have fallen victim to "craigslist pictures" before and will no longer base a purchase on a picture.
I would start with #2. Ad says "it has to go today so make me an offer"
Looks like a pretty nice setup. I wouldn't pay $500 for it. Assuming all drawers work well. Wonder what the drawer configuration on the craftsman top box is?
The first one
looks rather overpriced IMHO. There was a flawless, same setup on my local list for ~4 months for $600. He reduced it to $400 and it sold. But again it was freshly painted.
I don't blame you for not wanting to restore a tool box. Beyond cleaning / lubing. I try to avoid tool boxes that can't be used right away. Unless you have the setup and experience to paint lots of sheet metal. I have restored multiple machines and one small 3 drawer top box. Repainting the machines was SO much easier and less time consuming. Remember that internal rust can hold moisture and propagate even to your tools.
If I was in the area I would definitely go and pick these up though...
http://cleveland.craigslist.org/tls/3472594434.html
Best of luck. Let us know how it goes.