I would echo @Luka Milicevic in that your greatest challenge will likely be finding a deal that makes sense.

However, try not to fall into the common trap of over educating/analyzing.

I would certainly do that if it made financial and/or life sense. 

Does it make sense to hold the condo and rent it for a period of time to capture any tax benefits?

You still have to work hard and get a deal that makes sense.

And I didn't connect the Chinese drywall fiasco to the 04 hurricanes, makes much more sense now - I wonder if anything similar may be looming this time around or if lessons of the past have been learned?

Weird situation that makes no sense..

This is a common problem.

None of these seem perfect, but I am wonder if there are reasons one might make significantly more sense than the others. 

Have you analysis the deal and see if the number make sense?