My red flags were going up when you lumped it all together and said no SE :)I'd agree that if he is strategic and can substantiate "investment intent" per property then he's good to go.

I'm just strategizing.

I was in the air-force and had to have professional fire extinguisher training for our aircraft.

For example, despite there not being written exclusions, if an emotionally disabled airline passenger wants to to be accompanied in the cabin of the aircraft by his ESA and the ESA is full sized goat, the airlines will likely require the goat to be crated and travel in "cargo".

On a couple of the podcasts, I have heard guests saying that they strategically forego some of the available writeoffs to take advantage of the income on their tax returns for future borrowing purposes. 

Maybe if you were already awash in millions, and there were other strategic reasons to get those properties, I could see it.The biggest issue is, how are you going to stay in the game if you are losing money on your investments?

You can either look at it as:"I need to be as strategic as possible with every single payment I make to maximize the rapid increase of my score by playing with a complex set of rules" OR"I need to pay off my debts and build a strong financial foundation." 

Right now I am trying to be strategic.

When his home value dips below what he has mortgaged against it, he abandons it (strategic default) giving little thought to how that will impact him 5-7 years down the road. 

Three houses and 100K equity, start looking into strategic asset protection.