The key to being a wholesaler or investor is to have exclusivity.

The key is that the tax paying entity for the old property has to be the tax paying entity for the new property.

Being a general contractor and an experienced investor I see stuff from multiple angles and the key component of what you said was he is selling this property in the winter and that's exactly for a reason I've seen this happen many many times.

Would any of you all be able to share some insights on how you came upon a good property manager and what were some of the key questions you asked to make sure they were the right fit? 

There are also some key terms in the leases that are very important to address as well. 

That is the KEY, having an awesome deal allows you to go to family/friends/investors and show them how their investment will get a solid return with relatively low risk. 

Thinking outside the box is definitely key!

They didn't and I had to offer cash for keys to get them to leave.

We are interested in Turn Key, also interested in buying 1 family properties in different states in the US to rent.  

If the layout is good so that you don't hear or see each other (good privacy) and you get the right tenants: (low key/low maintenance-people you'd hang out with as friends) newly married that work or go to school all day and just sleep there make it a breeze!