If the roof is 30 years old, it is nearing the end of its life. 

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?

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.