Here are some general observations:-Is there any specific documentation that I should request for the damage of the property, if so- who from? 

You need to get to know the attitude and quality of tenant, whether they promptly report issue, to know how long of a leash you can put them on.I will give notice to inspect to check fire/smoke detectors furnaces etc. and while there insure there are no leaks in pluming, windows etc. basically make sure everything is working OK and have a friendly chat with tenant while observing the general condition of the unit.If I get a feeling of resentment from the tenant I simply explain I am a pro active landlord and am concerned about the maintenance of their home etc. etc.

That is an extremely good observation.

It gives me a great applied analyzing technique to observe. 

I would not confront them or even act outwardly like you know anything (your property is too vulnerable as are you).These online reporting systems allow you to give great detail, which you can collect just from observations (be it license plates, numbers, times, etc).While I have not totally solved anything (yes, they have younger trainees in waiting), I know one action took place ( one of two bad actors was arrested, slowing traffic by 1/2) and also it got them on the radar screen of authorities.

Great observation Nick.

My personal observation is, unless you have a friend or family member who has read and embraced the Rich Dad, Poor Dad cash flow concept, friend and family are the last ones to get it.  

Having said that:As Bill observed, I do have 2 decades of construction experience but very little knowledge of the endless constellations of legal minutiae.

It is by intaking all the data, as well as using your own observations as to what is happening in the market place.

@Toris Diggs i think your observations are exactly correct and the fact that most small residential property investors do not understand the numbers is what makes it such a great opportunity.