@Alf Holst I know a property owner who does this for one of their larger apartment complexes, so yes some people do it

Hi Justin, you have a complex financial situation, and your questions touch on detailed aspects of how capital gains and 1031 exchanges are treated in mortgage underwriting. 

Thank you in advance as we all need all the help we can get on the complex world of the tax code. 

House prices (unless you are talking very expensive homes or apartment complexes) are unlikely to drop $100K.

The investors who are preparing to buy their first property and don't have two pennies to rub together wanting to spend thousands on complexed entity formation for asset protection purposes. 

Let's say this is a 400 unit apartment complex.  

Sometimes simple is better than complex and in tracking expenses, simple is often the best approach. 

The schools ignore personal finance and business and hence people enter the world totally clueless as to basic concepts of business and finance.  25 years ago when I was financing small investors I made a loan to the purchaser of a small 12 unit apt complex.  

I did get an email from a young go getter who works full time at an apartment complex and does side work on nights and weekends.

The mortgage business is notoriously difficult, investor and lender guidelines (bank rules) are complex and vary among investors, generally speaking, brokers are not lending their own capital and the liaison on concierge gate keeper.