Do not do anything that does not produce income.

What this stems from is that the IRS requires that a taxpayer trace interest expense to the nature of how the proceeds are used. 

There are times when we see deals on the table that won't produce any cashflow or not enough cashflow to meet our target hurdle rate but the tax benefits or appreciation potential may make the deal attractive. 

He sometimes attributes his own good nature to those who do not deserve it.

Again, not blaming Roofstock because it's not necessarily their fault... it's just the nature of their marketplace and so many unknown element that can lead to things like this.

It has solar power, a compost toilet, and other things of that nature to be self-sustaining.

I'm just not seeing any strategy that can offset to any significant degree, the depreciating nature of either asset.  

I did buy a website which was expensive and produced nothing, still trying to decide what to do with that sunk cost.

Any comment made about a positive experience with him has been from an account with little to no information in it, or of some other suspicious nature.

A $500k property should produce gross annual income of +/- $50K but can generate as much as $65-70k with the right location and amenities like a hot tub.