The reality is that having everything "paid off" makes more sense later in life when time is not on your side, but if I were you I would be looking to invest in assets that allow you to create 50k in equity without scrimping and saving for months. 

Do you think the asset might be used up to pay or sustain his/her life. 

@Cesar Egas I currently work in Del city as a police officer and been around the area my entire life.

I worry about not prioritizing my wife, especially being pregnant, and family life.

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. 

Any ideas on other areas we could be looking at that will achieve a price point around $100K - $125K for a SFH in decent/stable neighborhoods with healthy rent rates?

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.