I finished all the degree requirements only to discover I was extremely burned out and had to complete another year of electives to satisfy a minimum number of credits at that university.

What I noticed so far is extremely high property taxes. 

SDIRA has been extremely accommodating in the setting of an eviction that occurred because the manager that they previously used neglected to tell them.

People even do this in Vancouver though it must be extremely challenging.  

Another example of this is Newark, extremely strict laws making land lording a second job.When finding the right area to invest, towns with more lenient land lording laws and proximity to public transportation tend to be a receipt for success.  

.- 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.

Chicagoland is extremely tenant friendly so understand that going in. 

And as I explained earlier, your investment is protected by real property, so your risk is extremely low. 

Btw, this kind of note-taking has been extremely helpful in other aspects of my life, and I imagine it will work quite well for real estate as well. 

An extremely detailed scope of work along with an extremely detailed contract, are the keys to a project that is going to finish on schedule and on budget, without surprises.