I aim to use real estate investing to build generational wealth, enable me to work a traditional job only if I want to, pay off my student loans, travel on demand, pursue dreams and to give money away to worthy causes. 

Section 8 adds a standardized lease, annual inspection and a subsidy to enable the prospect to afford your rental.You and Tenant sign your lease and the S8 lease. 

Doesn’t that make it impossible to get the full 15% step-up in basis enabled at 7 years?  

I know you have extensive management experience but perhaps that could be a compromise that will enable you to keep pursuing RE investments but not place so much stress on your husband? 

Both licenses would enable me to cover more aspects of the RE-investing ball o' wax.I have some hands on experience building houses as a laborer working for other builders. 

That would have paid for his education five times, and could have prevented his losses and probably enabled him to make greater profits instead of losing his shirt.There's an education-related real estate investor group which meets in the Lake In The Hills / Crystal Lake area.

That will also enable me to leave a legacy for my children and grandchildren.One of the guys in our office suggested that I start listening to Bigger Pockets and it was one of the best suggestions ever...it is truly life changing.

Instead, plan on creating a business through real estate that will steadily grow year after year, enabling you to meet your financial goals—and hopefully accomplish your dreams.

This will help you qualify for money enabling you to purchase a larger property.If you can reduce your cost of housing then house hacking is a win... especially in a high cost of living area.

Negative cash flow may seem counter intuitive but if it enables you to make a different high cash flow deal it would make sense.