I have no prior investment experience but after living in Paraguay, and reading some books about real estate investments, I think I'm ready to buy my first property.

I want to buy a 1 to 4 unit multifamily and house hack it (live in one unit and rent out the others).

Not going to live off that income.

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

Each tenant living in a building has their own unique rent amount, so even if they do not leave a notation with the rent payment, I know whom paid the rent based on the amount alone.

I know because I successfully owned properties in Phoenix while living in NYC and Houston.  

With your point, it seems like living security of 'where's next' for them will be the biggest obstacle for the seller to overcome.

I have an applicant who says she lived in the Dominican Republic prior to the 2 years she's been at her current address.

Its a rule of thumb SHORTCUT we use to make DECISIONS every day of our lives!

But it’s clear you’re a smart investor who knows the long-term benefits real estate can bring.I keep reminding myself why I stick with real estate: you can make money every month in four different ways:Cash Flow – Passive income to live on.Appreciation – Long-term property value growth.Depreciation – Tax benefits that reduce your taxable income.Tenants Paying Down the Mortgage – Even if you’re paid off now, this is one of the biggest wealth-building tools for leveraged properties.It sounds like your main struggle is the stress of active management—and trust me, you’re not alone.