I own one house in Morningside, but I wish I had more.That said, I've had plenty of opportunities to buy more homes in that neighborhood, but I've passed on all of them because I'm extremely picky with what street I'll buy on. 

Because there is a flood of new investors in the markets, the states are taking notice and adjusting the laws to make it extremely clear that wholesaling is illegal as it is taught.

Its in a appreciating part of Washington DC, which is going through extreme gentrification and rent in the same area go for 1900-3000.

They are not as distressed, look for stuff like single pane windows, older style of trees - there are several shrubs that were extremely popular in the 80s and are not popular now.. look for wheelchair ramps.

You only have to finance once, manage one property...I'm in an extremely hot market as well and people are jumping on top of each other to get a decent deal.

Other than in extreme situations you are going to be buying in war zones. 

I have not been anywhere close the extreme your describing but usually my all in costs are 25-40% LTV and my bank is willing to give me 80%.

The roof will not get an accelerated schedule, however having a cost and square footage broken out will extremely useful in the case of damage. 

Code office within city limits is extremely involved. 

The people who do it, support it and the people who oppose it are extremely vocal in their dislike for wholesalers.