My concern would be health and safety.

Rental inspections are common but really they are occupancy inspections focused on health and safety.

In other words, it's likely to lose money, at least for the first few years.As others have mentioned there's some measure of safety with property in an HOA, but there's also risk.

A safety net.

Trying o buy a few more by leverage but always try to have a safety factor with some paid off properties plus W2 jobs with a decent income to deal with economic downturns as happened in Detroit but not in Chicago, not yet. 

It's more likely that the lender is holding $5500 of the seller's proceeds in escrow at closing to pay for the repairs (if the seller had the money now, he'd probably have already fixed it).In my experience, when lenders do an "escrow hold back" like this, they base it on 2-3 reasonable estimates, then add a safety margin to that. 

A whole life insurance policy isn't just a safety net; it's a powerful tool for wealth creation (ref: other rich people and lucrative institutions). 

Health and safety?

One federal court of appeals held that such a blanket ban violated Title VII, stating that it “could not conceive of any business necessity that would automatically place every individual convicted of any offense, except a minor traffic offense, in the permanent ranks of the unemployed.”Although the defendant-employer in that case had proffered a number of theft and safety-related justifications for the policy, the court rejected such justifications as “not empirically validated.”

Do mid term rentals listed through airbnb still need a separate, formal lease, similar to how a LTR would be set up.. or is the airbnb booking enough and provide enough safety to the landlord (e.g., tenant doesn't pay, destroys property, etc.)?