Sorry to disagree with @Chai Xiong, but I think you are absolutely on the right track with your train of thought.

Many will disagree with my approach and say a faster approach is better, but I'm having fun with it and raking in great cash flow.

It seems that most of the above posters disagree about liability.  

The problem is that you're not allowed to do it intentionally.Also, I disagree with your attempts to plan for "after-Trump" taxation.

Inner city isn't affected by fluctuations like suburbs are because they receive more assistance so they are more stable investments even though 99% of people on BP are going to disagree only because of demographics.

I'm not a tax expert but all of us lay people seem to disagree with your opinion.  

I also disagree that VRBOers plan further in advance. 

While some contractors work on a 1099 basis, I worked as a W-2 for safe harbor reasons (the IRS has vague rules about who is a contractor and who is an employee -- picking the wrong one can get expensive for the parties involved when the IRS disagrees with your choice).I also had to learn how to live on a lumpy income stream as a contractor (if the agency didn't have a project for me to work on [no "billable hours"], I didn't get a paycheck).

@Corina Eufinger  I respectfully disagree. 

So hopefully you'll forgive me if I disagree with the fatalism of you and @William Jenkins.