Quote from @Erik Estrada: It's very difficult to time the market.

As an out of state investor, Birmingham has proven far and away my most difficult city to rent remotely (it's one of five cities in which I have rental properties), mostly because of terrible property managers.

Nothing is that difficult but there are a few things to know.  

That is difficult to answer because even within neighborhoods, there are B,C, and D pockets.

Of course we just had a few hurricanes, but that doesn’t make it extremely difficult to get insurance.

Mount Airy in particular is probably the most difficult neighborhood in Philadelphia to learn and there's no way you can do so from a computer reviewing rental rates and crime assessments. 

The main differentiator that I have seen is: 1) Asset class: Retail rarely even dipped in price and it's difficult to even say that it had a downturn.

I have decided to step into the world of property, curious to see what people here think of contract wholesaling.My main questions are:- Is it difficult to find investors after negotiating a decent assignment deal? 

This kind of "deal" usually means the property is going to be very difficult for the seller to sell in present condition - they owe more than it's worth, or the house is in bad disrepair, etc.

Once the lease is in place it becomes a little more difficult to deny the occupant from operating their business.