Get down to the basics and correct all the habits that have brought your life to where it is now. 

One of the reasons I want to get into investing, so I don’t have to work like this my whole entire life!

The quality of tenant is the variable, most people that need section 8 are good people who just haven't quite figured out how to improve their situation in life, they just want a place to live and will generally behave if they have a solid, clean, safe place to live.Make sure you check local laws and rules around section 8 so that you don't get yourself in hot water, perhaps get in touch with the existing owner/property manager and see what there experience has been with section 8 and especially the current tenants. 

I think I would take your parents money and invest it on impressing the ladies and having the best 4 years of your life. 

Where do you want to be in 10 years, not just in real estate, but in life?

@Agyei Axum i have been renting by the room for the last 7 years. that is actually all that i do. i would strongly suggest doing that in your case to boost cash flow in your expensive market. i would find comparables in order to price effectively.

Other life things got in the way of jumping in immediately.

I have actually seen your comments in many other threads regarding marketing yourself and avoiding the premiums of MLS deals.I periodically do a SWOT analysis on myself/my life.

I make an OK living but I want more out of life.

However, I've been around the real estate and mortgage industries my entire life.