I'm a former high school, and junior college football coach.

Do you have the experience to make sure you pass permit inspections?

My brother is about to head to college and I was thinking about perhaps putting a down payment on a triplex were he could live, after showing my parents the money he will spend on rent during his 4 years ( about 14400$ since rent around the university is about 300$) they have decided they could pay half the down payment (10k) if I instead don't charge him to live there.

I got a business degree in college with an emphasis on real estate.  

Has anyone gone through this type of process or has anyone tried re-permitting a property from a 2-3 unit property??

Permit it while keeping the tenant in the property.

If they pulled the permits but didn't get it inspected (RED FLAG). 

We have 3 boys, one is junior high, one is high school, and one in college.  

You should send college requests to your surrounding investors with a brief message about how you're new and and that any pointers or guidance would be greatly appreciated!

How hard was it to get a conditional use permit and was there an extra cost?