Hello all,I am a homeowner looking to supplement my income by purchasing a second home, preferably a duplex, and renting it out.

In this case, you walk into the sunset because your LLC has no assets, while the property owner loses his/her property and maybe faces their own liability if they don't have enough supplemental insurance? 

House hacking would enable you to have a lower downpayment %, plus lowers the reserve requirement to 1-2 months. 

And being that you're just looking to supplement your $15K, you may be able to get what you're looking for. 

I'm looking toward retiring from my 9 to 5 job in about 10 years, and want to supplement my 401(k)/IRA and Social Security (if it's still around) income. 

However, very, very few put you in practical, "think apprenticeship type" opportunities to learn alongside experts doing large, syndication deals enabling you to rapidly grow your experiences , knowledge and credibility in a safer environment (less bruises and broken bones) without damaging your pocket book and reputation doing bad deals in less than stellar markets. 

I work closely with all kinds of investors as my company provides self-directed retirement plans enabling our clients diversify out of the stock market and invest into non-traditional assets.

More specifically, I am looking for investment vehicles other than "playing the stocks" in which to generate long-term wealth and an additional supplement to retirement.

Audrey your aunt would not want you in danger for monetary gain.Find another way to help supplement the payment if your aunt needs it.How many more years of college do you have before graduating??

It is important to understand the basics (which should be easy based on you background), but solid educational foundation will enable you to quickly analyze properties and know in a matter of minutes if a deal requires further analysis.