Any option to subdivide the lot or put something else on it that could produce additional income?

@Bosko Mijatovic Especially for a job like that you will want to pull permits, un-permitted additions absolutely destroy the value of a home in many circumstances not only do you lose the money you spent to do it but you can lose the cost to fix or revert the addition. 

The company who set up my first LLC, included additional documents like certificates for members, minutes information, etc. 

The basement was unfinished, so we were able to add some square footage as well as a nice additional living space.

To name a few:Base your underwriting on how you will operate the asset, not based on how it is currently operated or based on the broker's pro formaCreate a budget for each year you plan on owning the property + sales assumptionsHave an upfront operating account fund in addition to ongoing reservesBased the market rents on your own rent comp analysis, not the broker's rent comps15% contingency on top of interior and exterior rehab budgetConservative annual income growth assumption (no higher than 3%)

Additionally, this would give you experience in property management, however, a bank might not like the fact that you want to use a loan product (HELOC) to open up another loan product (mortgage).

Your biggest goal right now should be getting a decent W-2 job (assuming you don't have one yet, but if you do, congratulations again) to justify both your college debt and additional debts to secure real estate.

Additionally, he is probably not motivated to leave since he is living for free right now.

@Mike Dorneman that was my thoughts exactly, would be to find a partner that has a process in place and bring additional funds to the table that would allow them to either move into larger deals as you mentioned or a greater amount of units in a much shorter time frame.  

Purchase price: $300,000 Cash invested: $15,000 Bought this house purposely close to a college and lived in one bedroom and house hacked the additional 4 rooms, Dropping my house expenses down to approx 200/month.