Once you are familiar with what banks typically ask for, I'd recommend making a folder of all the needed documents.

Looking around online it seems other condos in the area are renting for $1300-$1400 a month.

I would go to the meeting and document the actions you took and ask for the fines to be waived this time.

However, if you buy a primary residence, live in it for 2 years and then convert it to investment you can then sell it within the next three years and take both the 121 exemption and 1031 the remainder because you are selling an investment property and you can still document that you have lived in the property as your primary residence for 2 out of the previous 5 years.Regarding your last question - again you cannot 1031 a property that is currently your primary residence even if it was investment at one point in time. 

There are a lot of PM software systems that allow you to bill and collect rent online.

This, coupled with an online portal and rental capability along with utilizing a call center allows me to manage the properties from home for the most part.

In your opinion, what documents should I ask for?

Purchased and began my online real estate license course (via Kaplan). 

You will need to have a partnership/operating agreement and will need to file several documents with the state. 

There is free software out there that will effectively market your property, screen tenants, price your rental based on comparable properties, provide renters insurance and online applications, etc.