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. 

Sounds to me like you're about to watch $50K magically disappear unless of course, it comes with a bridge.

Unfortunately, when a city grows it has growing pains, in this case some very classic homes don't fit in the cities blue print.