This then allowed me to buy apartment buildings, which have been much better pure investments than most house hacks in my area here in Chicago.

In the end, I feel like this is purely speculation.  

Are you thinking you will eventually turn this into a pure investment property and hold long term?

Can Pure PRINCIPAL ONLY payments (were you are not paying any interest) he deductible and / or used as an expense to offset other income earned.

I love the proximity to Battery Park. 

If you hope for large capital gains, it’s pure speculation.Foreigners buy in Montenegro because it’s cheaper than Croatia.

If your time is worth $50 an hour and you spend two hours a week answering calls, coordinating cleaners, or whatever, that's $400 in your calculation.You'll hear people on BP say they have several rentals and it only takes them 5 minutes a week to manage, which is pure bunk.

Show up to "Change " the batteries in the smoke alarm and look at the kitchen and bath and do not let dirt to pile up.  

He said the app will notify you when there is a ride available to take, but he just ignores them while he drives and only a handful of times he has taken a customer, purely because he noticed they were going to the same area he was driving to, basically along his route. 

@Jeff Lara are you going to owner occupy or pure investment?