The answer is - YES - if you get them a legit P&S package - the property should have a enough equity for a flip - or under water for a short sale. 

No need to muddy the waters. 

Have you advised the tenant that the dirty water resulting from the powerwash would dirty up the windows?  

Call the local water company they will tell you. 

That said, what didn't pencil was the over-valued land price, the cost of running electric and water hookups for each of the houses over 40 acres, land-clearing and excavation, and the amount we anticipated people would be willing to pay per night extra for glorified camping.  

It's a 3/2 lakefront property (more like man-made channel-- no boats, fishing, or swimming), and the minute you open the front door, you see right through the house to the water. 

What this effectively would tell me and the argument I would want my attorney to make is that you did this purely to establish a higher degree of anonymity from you tenant, but never actually had the intentions of running a separate business entity. 

They are all slightly different...some pure networking, some educational, etc. 

So if you were worth 2 million and bought a house 50k cash that is a 2.5% total of your portfolio value.Maybe dip your toe in the water and see how one goes first.

Again, I've never bought or sold a piece of real estate in my life and I've just put my toe in the water.