Some may see it as negative i see it as big picture, real world questions.I'm just a decade or so behind you i would guess Rich, and live in Florida in involved in real estate investment since a child as my Mom owned rentals and was a Real Estate agent.From your bullet points1.

There might be several reasons why the family is holding on to it— in California given the parent-child exclusion for property tax reassessment and prop 13, if a property was bought years ago, the property taxes on an inherited property could be incredibly low that a lot of families choose to keep inherited real property within the family instead of selling, especially if it’s paid off.

On the other hand, if the son just turned 18 and has been living in the apartment with mom since he was a child, I would not require an application (and you probably don’t have legal grounds to force him to complete one in this scenario). 

Life is a little more complicated now with a wife and child to contend with.

Not an ideal situation but it is what we agreed upon with child care and the situation that was at hand about four years ago. 

That seems fine to me because I know there is a market for that--young singles, young couples and even possibly single mothers with one child.

that 100k will be our down payment for our next home which will place our next home's budget within the 350-400k sale price...the X factor is my wife is pregnant with our second child. 

My daughter was born two months ago, our first child, and I want to be able to have freedom to be with her whenever I want as well as leave her something for some freedom of her own when she gets older.

Now the client has a new born, his wife no longer works and as they are on a single income for the time being, they may not be able to qualify for a mortgage.

This sounds like a recipe for a family fight later unless you are an only child.