I just feel like going deep into rabbit holes like this aren't worth my time and effort tbh.

Now he has to make choices and put forth the effort to live his most rewarding life.  

If you're applying for a Conventional/FHA/VA/ or USDA loan, then they will do a "global cash flow" where they take into account your PITI (Principal + Interest + Taxes + Insurance (hazard and flood) on all properties (second mortgages included), HOA payments, car payments, student loan payments, credit card payments, and installment loan payments in the numerator and your gross income in the denominator.

I'm also investing in ABQ and looking to expand my efforts there. 

While rent prices are expected to rise, the increase will be modest, reflecting broader market stabilization efforts and economic conditions​.DisclaimerThe information provided in this forecast is based on data and analysis from multiple sources.

As they should be, it takes more effort to wait for inspectors, make repairs, ensure rules are adhered to, etc. and that should be factored in.

No cash flow real estate investing can be frustrating to newbies... you are doing all the work, and not seeing any 'pay' for the effort except on paper where you property is worth more.  

Not sure how far you are from Chicago proper, but the ULI (Urban Land Institute) is a global group with chapters in most big cities. 

In 10 years, when you have a nice portfolio of homes and they're cash flowing nice chunks of money, you'll appreciate the amount of time, energy and effort you put into your business and will get to enjoy the fruits of your labor.When I first went to the cpa I've been using for the last 5 or 6 years and explained what I was doing, he said, he's heard it before.