I am looking for what sort of questions I should ask, numbers I need to find out about, strategies that I could work with to help him not lose (horribly) on a deal with me in which it seems like the house isn't worth what they paid for it...

It's horrible.

  $410,000 is a horrible number (Just like $399,000 is a horrible number, etc.).If they lower it to $400,000 they're opening themselves up to a whole other market.When prospects search online, what do they search? 

Another hat I wear being a physician, which are just as horrible at standing up for their rights from a political standpoint.

The numbers are horrible on this as a rental.

@Shavers Lawn Not a horrible plan.

We looked at a foreclosure one time, the stink of dogs was horrible.

Our property manager was horrible so I fired them and thought we could manage it ourselves since she was such a "great" tenant.  

This town was a town that I enjoyed visiting as a kid, but due to the economy and horrible decision making by the local government, the entire place is in shambles.

My neighbor just had their pool tile replaced and two workers that couldnt speak english did the work and it was horrible.