He may get stuck with rent control laws that prevent him from catching up later. 

Even though the distance would be a lot farther to travel than initially investing in another Chicago neighborhood, I know the tenant laws are a lot more relaxed out in the suburbs, the average price of property is much lower, and it just feels like a smoother entry point than a large city in general.I'm very interested in multi-family properties to begin my real estate journey and have worked on putting a team together, so I am getting closer to actually acting, not just observing.

I'd try to understand landlord laws in each market - i.e. figure out which markets are more landlord friendly.

This log will be invaluable in case of an audit.3.Grouping PropertiesWhile I’m not an expert in international tax law, my understanding is that you can group all your properties together for material participation purposes.

Being kind to your in-laws can go a long way in many areas.  

I'm not familiar with TX law.

Context matters, and there are steps you can take to protect yourself while still giving applicants a chance to prove their reliability.ALTHOUGH, still stay compliant with all of your states Fair housing laws, Always.

Read a text on real estate principles, law, and finance.  

I do not want to stretch into California due to the Landlord laws and taxes. 

I must abide by the law and trust that mandate enforcement occurs even though I don’t see signs of it.