I've hired hundreds of contractors.)I only know what you've posted but it seems to me you may be being too harsh? 

I will be negative 500$ on the monthly cash flow.The property is a duplex.

But it looks like you might be negatively cash flowing with 15 year mortgage!

I tried to get my parents to let me take a gap year but they insisted I go to school immediately and I only stayed there for a semester because I didn't have money and couldn't find a job while I was there so it didn't make sense for me to stay.It's not necessarily that I think college isn't smart, it's more that the standard recommendation when talking to high school seniors should be more along the lines of, take some time and actually figure out if it makes sense for you.

With financing of 80% or less it's a negative cash flow.

@Demarcus CrumpI’ve been analyzing deals in my local market and most asking prices on MLS for 2 families tend to have negative cashflow and ROI.

If you have a cash flowing asset you can hold onto it indefinitely, if you have negative cashflow and are hoping for appreciation you will end up being a forced seller in a down market.

I only charge $100 tho.

Yes you are buying near a peak and over paying for the area you are in, but if it meets your family needs and you are ok with those negatives then pull the trigger. 

So the experience has been pretty negative so far.