I am 23 years of age and very new to the real estate world.

My oldest install is 16 years old, I'm currently turning over the unit, and the floor looks pretty good, as does the 15 year old floor of my son's room that he moved into at age 3.

I have two step-sons about your age (I think) and they're very confident with some things- but not paperwork!  

At their age they need to place it in a secure conservative income fund.

Having 5 properties at your age is nothing to sneeze at! 

Not all towns require a C.O. for every property depending on the town rules and the age of the building.In the case of this property, the seller is trying to make the buyer responsible for the CO and the certifications. 

I am willing to work extremely hard to help my father have a steady steam of passive income by the age of 60 -- I believe he deserves that at the very least for all the years of hard work he has put in and the outstanding life he has provided me regardless of hardships he has had to face.

@Madeline jI would continue to maximize your 403b contributions but keep in-mind that you generally won't be able to transfer those funds to an IRA until you either stop working for that employer or reach age 59 1/2. 

I would make note if a roof needed replacement, ages of systems, photos of and description of damage.

We aim to make 100k a year in income by 30 years of age.