You think you should be able to choose whether or not you put the financial system at risk (by not having health insurance) and believe that it is your prerogative to burden the system with unexpected and unplanned and uncovered expenses and that government should mind their own business and let you play.

I rented the first property to a family with a special needs kid who has unplanned/not schedulable medical issues. 

If you have a large property, you are more likely to encounter things such as unplanned property maintenance and repair, longer-than-expected vacancies or expenses incurred by irresponsible tenants.

Repair Costs: $47,610 Holding costs: $6,300Closing costs: $11,150Staging Fee: $2,300Total Pay Out: $37,640Construction Loan hold back: $29,000Insurance Claim $12,529 (Roof damaged in Wind Storm) unplanned replacement and tree removalBank allowed me to keep my 20% down payment at closing, which would have been $15,000 due to total amount requested for repairs being $44,000.

It is still painful when you get a sewer and an unplanned roof at the same time, but is still doable.I am with @Jonathan R., I could NEVER do a $550 per month repair budget. 

So while you may feel comfortable knowing that you have full vacancy, a deployment can quickly create substantial unplanned vacancy, while reducing the population of available tenants. 

That 84 unit property by the way, 364,000.00 in excess expenses, un forseen un planned.

This is instant return to your family and if you eliminate 18% interest on a credit card, that is a hard return to match with the amount of effort it takes.Third, I would make sure you have an emergency fund so that you can pay for any unplanned expenses that arise.You can focus on the highest interest rate debt first, which makes the most mathematical sense, or you can eliminate the smallest debt first for a feeling of accomplishment (Dave Ramsey method).Also, I am a firm believer that you cannot cut your way to prosperity.  

This was an incidental, unplanned event where ultimately I'm looking to do maintenance on these properties.  

This was an unplanned occasion.