Now, you need to figure out how to find deals and pay for them.

If your brother is looking to invest in real estate largely from a tax reduction standpoint they should pay a qualified real estate tax strategist to review their specific situation and what may or may not work for them. 

The garage and the fact that a long term tenant was in place paying market rent.

If a tenant causes a claim, why should the landlord's insurance pay - possibly resulting in an increase in premium or even a cancellation of the policy?

More than happy to partner up or pay for the deal itself.

Also, if you are a minority, WRA has the Partnership for Success program, which helps pay for your start up costs.

Long Term non-paying Tenants.

My profile has my YouTube channel and I have an episode that shows you exactly how to create the comp set and look at amenities that matter, what others are paying for cleaning and how other listings look - that way you can see how to best market your property. 

Our current mortgage terms include a late fee after 5 days, so they’re already paying extra each month and have to split the total monthly payment up between 2-3 payments when they get their pay check.

I would stay away from section 8, pull credit and background, and call referrals, and look at pay stubs for everyone who applies.