My area has many multi families that are quite old so if you can focus on newer or even new construction and still make your numbers work to me that's the best and lowest risk way to implement the house hack, but for sure do it! 

This separation prevents disputes and keeps coverage clean.My friend finally saw the light and asked for a DP3 coverage on his rental.  

If you are gonna drop $20k on something, drop it on a marketing firm to create the business plan and who you are going to target and then implement the plan that is specific to your business.

I started advertising, improved security, invested in better lighting, added automation, and implementing technology which made doing business easier for the customer.

It is the same reasoning as the wholesaling law, to prevent the amount of unlicensed predatory behavior from the consumer, ultimately raising the standard for roofers.

Some of my most successful clients that have strong cash flow, implement these strategies. 

The only thing that works is learning, implementing, learning more, tweaking, and putting in massive amounts of work.  

Spending the time and taking the time and energy upfront to screen really well, meet and interview the tenants is absolutely a key to having the best chance as a "smooth" property in my experience.as a side note on "issues or problems" in general....I feel like the problems we think we will have as landlords or owners never seem to be the actual issues that come up, you can plan and prep and preventative maintenance to the cows come home, but something will come up!  

A quick walkthrough can be the difference between a minor fix and a major expense.Lesson learned: a short visit today can prevent thousands of dollars in damage tomorrow. 

Finally, since you have very few degrees of freedom on the income and expenditure nexus, you may want to pay particular attention to preventive maintenance to help avoid getting hit with a big capital cost item.