(I can identify with that.  :-)   But truly, digging for information is one of the best skills that you, @Aaron Coplin can develop. 

However, the path of least resistance may lead us down the road that we wish we would have never traveled.  

If there is negative equity then the same dollars identified by that ratio will be a lower UPB percentage number.

Honestly, the more questions you ask, the more questions you will be able to answer down the road. 

Do some online researching about the economic realities, then plan a big road trip and check out a bunch of towns.

I had some REI knowledge but you basically paved the road to me and my families real estate investing strategy.

Leave the cosmetic stuff for down the road.  

I want to know what processes sophisticated investors use to identify a cash flowing market?

I do happen to believe many 'wholesalers' are basically brokering, and I suspect as we see more people that get into it and do it wrong that we'll see some legislation of some sort start to come in play down the road.  

But you need to show that you had the intention with some documentation, like a signed lease for the property, newspaper ads, craigslist ads, photos of for rent signs on the property, etc.And unless you do another 1031, by selling the 1 property you'll owe taxes not only on the 1 property sold but also a portion of the gain from the first property relinquished in the 1031.An alternative would be to suggest to the buyer a rent with option to buy or some other mechanism to both show rental income as well as deffer the sale until year(s) down the road.