If you are considering this approach, I suggest you buy an A-class property in a landlord friendly city and get a PM.

Since this is my first project, I’m very open to any advice or suggestions—especially regarding potential obstacles I might not have considered.

Make sure you account for all of your interest load if youre using a Heloc for permanent financing as you suggest.

When I maintained my position that I wouldn't be paying 10K up front, Dmitri then insulted my section 8 investing knowledge and suggested that if I wasn't ready to move forward, then it was because I didn't understand enough about section 8 to begin with.

She suggested a much lower price than I would have thought of offering, and the bank took it.

Use this time to study at the university and continue to study real estate.

If credit scores are fine, and you are just new to the work sector, then I would suggest doing a conventional loan with a strong income "non-occupying coborrower". 

I had to have an awkward conversation with my favorite realtor when their broker suggested everyone had to pay a $700 “document fee” on every sale.

@Mary Parsek you are pretty close with this forum but I would suggest posting this in the "Mortgage Notes" forums.  

I would suggest to sell the condo and reinvest into a single family home.