Aside from how painful it was to get our real estate agent to prepare a satisfactory lease that protected us (she said it was compicated), she told us that according to the listing agent the sellers felt the rent was too high because it was more that their current mortgage.

Lack of maintenance was a bit of a pain toward the end, but it was also great to have dirt-cheap rent and lots of freedom (wanna paint the walls red?

My gut feeling is that these people will be a pain to deal with.Do I even need to provide a reason for denying them?

What are their pain points?

Here's the painful truth: that kind of info isn't readily available.

This will give him the staying power to hold out for a good renter vs accepting the first one that comes along waving cash at him because he feels the pain of having a vacancy or two. 

(And VRBO with their new structure has NO rhyme or reason to what they feature- a newer property of mine was featured all month while my older one with 50+ 5 star reviews was at the bottom of the heap) It is a bit of a pain coordinating both in terms of changing prices and I am starting to look at 3rd party solutions for that. 

You will have to start though with getting your business/rental license and all that and get it licensed as a rental before the eviction, which can be a pain in the but if the old owner doesnt provide access to the propertyI personally would not purchase an REO in DC if the owner has not vacated.  

Jennifer - all great questions and I feel your pain in being "a little lost with everything".  

Recently I had to coordinate an entire kitchen repair due to a broken pipe, That was a pain, but I was still able to do it remotely.