Is your goal to use being an agent for your own personal investments or actively try and grow your agent business to eventually leave your W2?

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

I took two business law courses in college. 

You can probably make up for the perceived loss through the reinvestment in your US business.

If you are using STR, REPS, or self rental with material participation to convert to active or nonpassive income, you do not have to do this if you have passive business invesment that produce passive income that will exceed the loss generated by depreciation.

The vacation side is more of a business and requires a lot more work but the affordable housing side is less labor intensive. 

They must be very low odds because insurance companies are in the business of making money, not paying out maximums.

My opinion is a lack of business organization.

Quote from @Joel Oh: Your business must make money day 1.It is so much more difficult to fix the model that is not making money than starting a new business that makes money day 1. 

Thats why you see very few HML that were in business prior to 2010 to 2011..