Sometimes simple is better than complex and in tracking expenses, simple is often the best approach. 

The schools ignore personal finance and business and hence people enter the world totally clueless as to basic concepts of business and finance.  25 years ago when I was financing small investors I made a loan to the purchaser of a small 12 unit apt complex.  

His living there is, IMHO, a HUGE complexity.  

The mortgage business is notoriously difficult, investor and lender guidelines (bank rules) are complex and vary among investors, generally speaking, brokers are not lending their own capital and the liaison on concierge gate keeper. 

Chicago is a complex beast of a city with literally hundreds of suburbs, each having their own nuances.

On the other hand, separate LLCs for each property provide better protection but are more complex and costly to manage.

I have 2 properties in PCB and i live in Atlanta.key thing, you absolutely have to have a great cleaner. they will make or break you.then other things, maintenance person, know your emergency 24 hour service people (plumber especially), and contact if you are in a complex for example.then there is technology stack that can help you automate things. if you do a search in this forum, the tech stack is asked quite frequently and discussed

However, I just found out Easy Self Storage started to sell their own access hardware, and then it released a new feature on their software/website that you can see gate access activities/log live and can even open/close the gate remotely simply through the website (even on your mobile!).

I am also seeking a CPA who specializes in the complex world of real estate investors.

But this model would help in getting together the necessary funds (especially for a down payment and minimizing the potential interest on a loan), while bringing in legal complexity.