If you are considering renting it for a minimum of 30 days, I believe you will be exempt from any short term rental rules and taxes. 

Eventually, after finally admitting he could not obtain a loan, he failed to return my capital, and completely stopped responding just long enough until the banks were unable to reverse any payments.

A friend of mine invested in one last year—apartments upstairs, a small coffee shop downstairs - and the combination of income streams made it a steady performer.Scaling with a 1031 Exchange:While not applicable unless you sell a property, planning for a 1031 exchange could help you scale quickly while avoiding capital gains taxes.

We owe $154k on the property and the interest rate is 4.25%, the monthly mortgage is $1050 with taxes and insurance.

But I also love the idea of investing in real-estate and utilizing its tax benefits I have read around 10 ish books or so and the one I am reading right now recommended this site I am looking for some advice of things I can do to either prep for an investment into real estate and or do right now.

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

@Luke H.Hi Luke,  As a private money lender myself I will focus on one element of your deal---5 years is a long time to be finally paid. 

Would the federal tax liability be $140k at year 5 for the sale, with long term capital gains (ignoring any Net Investment Income Tax)?

So, instead of paying taxes on $50K, I'm paying taxes on only $21K. 

This should include potential rental income, expenses (including property taxes, insurance, maintenance, and potential vacancy), and your expected return on investment.