And @Natalie Bender is right about spreading your risk by going into multiple DSTs. 

.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

Taylor sent multiple email inquiries to our insurance provider asking what risks their policy covered.

I want to be able to find potential markets/listings nationally based on the return. 

Throughout my career as a real estate investor and CEO, I have learned valuable lessons on maximizing the potential of each unit in a property.

Some may require a waiting period of one to two years before leasing is permitted, while others may prohibit rentals entirely as outlined in their bylaws.Always know the property’s potential for annual rental income and ensure the numbers work.

In terms of other factors, I'm not sure there's a lot because I did have some people express interest in filling out an application before, and I actually got really close with one potential tenant, but it was because of the alcohol policy that he ultimately decided to back out.

How would you manage risk? 

How much less will a potential buyer pay for the house, now that one "bedroom" does not have a closet?

The risk and effort is too great.