I'm worried about incurring student debt and ultimately holding back my RE goals.

There's a ton of college students just trying to make a quick-buck in this particular industry, so you may have to do some sifting to get to the real experts.  

I'm a 19 year old college student and I really want to start generating income from now and set my self up for success when I'm older.

To set this up and cover yourself correctly an attorney might eat up most of your anticipated profit with fees.Once you take the fees into consideration you wouldn't be getting 20% return even if it materializes.You could ask an attorney to co-participate in the upside and make no money on the front end but they might not go for that.

I'm currently a 19 year old college student.

I also felt that that there is a large student population with Yale, SCSU, Quinnipiac, Univ of New Haven and Albertus Magnus all in  and around the immediate area of New Haven. 

I am 25 years old, still living at home (with parents), college graduate (wonderful student loans), and looking to invest in my first multifamily property within 6 months; my focus is buy and hold investing.

Good credit score, only student loan debt, but not much credit either.

Volunteer the house as a project for a local high school shop class to come and work on the house, you supply the material they supply the students to do the work. 

I'm the broker for a SoCal student property management company and one of my clients is a partnership between 2 investors, one of whom just decided to pull out because he doesn't think their 2 SFRs are cash flowing enough.