If he has coverage, his agent can email you a certificate of insurance. 

Since KS is a mortgage state and the property has been sold at auction, you are in the statutory period of redemption and do not technically own the property, but hold the certificate of sale/purchase.

(Nice guy, However, he does not strike me as the type of person who keeps records)  He said he does have led certification certificate for each property.  

An estoppel certificate fixes this problem.

So my duplex in Philly is currently vacant (other than me since I’m house hacking) and i’d like to get the other unit rented out as soon as possible. I didn’t know until much after closing on the property that it did ...

Just waiting on my completion certificates so I can send those to my "sponsor" and sign up for the exam. 

You can either increase income by finding income that was under reported or inaccurately reported on the loan or you can find a coborrower to blend the income and lower your debt to income (DTI).You can pay down debt that has the highest payment relative to the balance so you can thin out the DTI.You can slap a MCC on that loan which is a mortgage credit certificate (if you're a first time buyer) and this is an owner occupied loan.

I honestly don't see a need to pay for those courses, I rather invest that money on a certification that would help me in the Real Estate Investment world.Also, I will definitely read up on HUD's and the new changes.

It's absolutely INSANE how much information you'll get for how little cost, and this will easily place you in the top 10% when it comes to knowledge of managing a rental property.And finally, if you're really serious about it you can always pursue education or certification options that will really cement your status as a property manager.

Look into a tax certification from "Tax Title services".