Are you interested in a specific startegy (brrrrs, flips, vacation rentals, etc)?

If you are considering this approach, I suggest you buy an A-class property in a landlord friendly city and get a PM.

I am still living in Chicago but plan to move to New York in a year or two.

We live in a litigious society and people are sadly looking for ways to either get something for free or more. 

It's a really sexy application on webinar, but even for the "Get It Now" price may not be worth it if you can't shut it off in a timely manner.  

Any of these will leave you in a much better position for success, and provide a greater income while you learn.  

House hacking in a 4-bedroom here could absolutely work if you run your numbers carefully and stick to those “higher-end lower-end” neighborhoods.

Scenario 1 they don’t or refuse to move- eviction costs and/or lost rent Scenario 2 they move out and Cap ex and turnover costs, lost rent, advertising for new tenants in a somewhat of a qualified tenant shortage, headaches can be avoided by simply having a conversation with the tenant to see where their head is at, and that they understand what your expectations are.

One very important point, in a subto that you sell on a wrap, you no longer own the property.

However, a lot of concerns can be mitigated with looking at their past rental behavior in a lot of different settings.