It is now fully rented.

I have a heloc on my personal home for 200,000 but ive only used 16,000 of it.

Here is my Cliff Notes on this elaborate example:If you have unused losses from the past, they might significantly soften the tax blow from a profitable sale.I don't see how this is called "strategic play" or "premium lemonade."

@Danielle Levy a lot of questions regarding your accusations:1) What are the average Days On Market (DOM) for rentals in this "hot" market?

From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

You need 6" clear from ground to bottom plate, and ground must slope away from house...5) Any place that water can enter the house (doors and windows, skylights, where roof meets eaves, etc...) should be checked thoroughly, if it's not raining on inspection day, you have to be really careful with this...any suspect areas, put a hose on them....

I have a property (fix and flip) under contract, but now, shoot, the REAL work begins.I am located in Milwaukee, WI, but my property is in a near suburb of the city.

Is this a person who is, from here, going to turn their life around from the desperate situation that they find themselves in right now, such that they are willing to take a Subject-To deal? 

I live on a very busy street as well.

Finding a duplex in Anne Arundel with 1 deed is like looking for a needle in a haystack .