I'm guessing you have considered this, but one way to get the benefits of rental ownership and still have intermittent access to your property, would be the Air BnB route.

Luckily the realtor tried to show the $1200/mo Hoa as a benefit as I would have “full use of the casino amenities...” less than 5 years later I didn’t buy the equivalent condo for $200k. 

The first was adjusting the price differences.

What other careers within real estate do you know of that benefit from having your license?

They could consider doing an exchange to a DST which is 1031 exchange eligible, but would provide managed real estate (completely hands off), but they still get the income off the DST along with the benefits of real estate (such as depreciation).

@Jason SternThe Solo 401(k) is going to provide the maximum benefit as far as deductions and flexibility with future investments.Since you are maxing out your $18,500 contributions in your current plan, you would not be able to take advantage of employee deferrals in your own separate plan. 

You can probably get away with spending $10k on drawing up legal docs if you put in legwork, this simply needs to be adjusted in your proforma, along with exit strategy(ies) and so on.

There are so many benefits as an investor to having access to MLS, comps, seeing any property any time I want, negotiating with listing agents myself, etc.

That is especially true with the tax law change that went into effect this year; the standard deduction nearly doubled, so the taxes you save by itemizing might be much less than they were in the past (in other words, because you are getting a larger benefit through the larger standard deduction the "cost" of not having the mortgage interest deduction might be less).I can see an argument for there being better uses for your money than to pay off a mortgage with a 5.5% interest rate (if you can make an investment that pays at least 6% for example), but if your quality of life will improve because you paid off your debt and are now "financially independent" then that is what you should do.

Then you can adjust it accordingly.I would also have Repairs at 5%, PM at 10%, and Misc at 5%.