He doesn't have any signifcant savings (~10k), and his only income is social security and a small pension which comes out to a total of ~3k a month.  

I sold a few homes in Jackson MS to Naca buyers.. its a process and the homes had to be in perfect condition before naca would close  IE FHA or VA appraisal standards at the minimum.. the program is designed for first time home buyers or low income home buyers also NACA was very firm on us ( the seller) buying down rate and closing costs. 

A structured installment sale is a highly beneficial tool when looking to exit an property (investment or otherwise) because it'll lower your taxable income and is customizable.

I have been renting during my whole college career and made some income through internships that I would like to use towards putting a downpayment on my first property.

The other founder and I have corporate real estate experience (Commercial Real Estate IB and real estate PE internships) but are not experts.

I wanted to house hack and purchase a property that has dual streams of income.

I agree.I don't think the golf simulator will guarantee you extra income, bit the ADU would get rate extra cash.

It seems like if you are trying to sell an income generating property but refuse to disclose any information about how much income the property in generating, you are probably running a scam of some kind?

Obviously, the interest I earn from lending would be taxable income, but how would the initial investment be treated for tax purposes?

OCF provides an online web portal to view and track all the rental income and PM managed expenses per property.