As a final question, would you convert a fully dressed out man cave with huge fireplace, full wet bar, half bath, closet, private entrance measuring 500 square feet into a mother-in-law Studio?

Your business/REI analysis (your current situation) based on your current financial situation and goals (your plan's timeline criteria), tells you what your "entrance" can/needs to be.  

4 - What is the Entrance Criteria for the following steps (after you buy this/these properties)?

It’s kind of a smaller backyard, the yard is fenced in and there is a deck with locking doors that is the only way to come out from the back entrances.

First, Put a 'three day quit or pay notice' on the entrance door to the property being occupied by this individual! 

I knew I could get $1400 a month on the deal and there are new developments going up at the entrance of the community.

Place clearly in your lease agreement that tenants are not allowed to make changes to the accessibilities of the rented property, this includes locks and entrances because of the possibility of an emergency or the necessity of an inspection by the landlord or official inspectors. 7.

The home has an attached mother in law suite with a septate entrance that can be used as a stand alone 1 bedroom rental.

I am worried if I buy a house that has 2 separate entrances top and bottom that neighbors will call the city since parking is tight and then ill be stuck with a rental that can't pay for itself. 

Some are on the courthouse steps...rain, snow, sleet, 110F, 20F, some inside the entrance, some in a courtroom, some at the annex, some in a tent near the courthouse, some in a hotel ballroom.