My parents funded college for me and that is the one major gift I know I will fund through the next generation.However, how to teach great money habits?

Its not doing much sitting in the bank/ stock market/money market funds.

There is no shortage of renters out here and Section 8 is my personal favorite for my own properties.  

The trick is to not take things personal.

Don't know where your rental property is, but in Florida, we have a statute that deals with death of last remaining tenant and the procedures to follow to allow the landlord to take possession of the property and dispose of the tenants personal property.

Though personally I'd want you to get your financials dialed in if they aren't already. 

If you plan to expand your portfolio, starting with a 4-plex might provide a stronger foundation for future investments.It's also worth consulting with a local real estate agent or financial advisor who specializes in investment properties to get personalized advice based on your financial situation and market conditions.Best of luck with your investment!

Then use the funds to purchase another cash flowing property. 

U have to put your own money into your retirement accounts no matching funds. 

Funds clearing banks is part of the business!