@Conor Murphy Please don't take this the wrong way but it appears to me that these are all questions that your agent should be able to answer relatively easily. 

Finally, there will be random repair charges from time to time, but think of how much time and money it would cost you to go out and change an HVAC filter.  

So you easily left $800K on the table by owning out of state properties.

Where is the dividing line where on one side you could easily do these tasks but are too lazy, as opposed to you are getting in the way of yourself if you don't pay someone to do it?

My designer is able to have a rough drawing of the place completed by the time we leave the house and with a measuring tape we can get all of the dimensions easily.

You could easily eat up 10% of your profit, leaving you with a 20% spread.

It could very easily cost me 20k to fix these situations so I can get my money back. 

He could have walked away when he owed $100,000+ and the house next door sold for $4,500Since he purchased in 2006, he has easily paid $10,000+ in MIP(Mortgage Insurance Premiums) and probably $1000s in above market interest to the lender.  

My tentative assumption is that yes, they could be successfully evicted, but it could easily take months.  

In addition, I think there is simplicity in "save money build credit" and is something to be long-cherished and shouldn't be overlooked too easily.