As with any branch of RE, you need to educate yourself, get 'good' advice, and have deep enough pockets to ride out early mistakes as you learn.

Also, hailing from Champaign, IL so if there's any state specifics in relation to these types of transactions (I'm more SFH), I thank you for any input you may have. 

Perhaps one that advertises that they handle hail damage.  

It's been a real treat to ride my vintage mc out to jobs to do and meet interesting people/situations! 

As of now I am a senior in high school with good grades and have a good shot at a full ride scholarship at my state college.

Welcome Hojin and best of luck on this addicting ride called REI!

In terms of big impact on our costs, ice storms and large hail (grapefruit sized two years in a row) have affected us more than tornadoes.Our top concern was that we could not cover more than $1,000,000 in gross property value without going to underwriting which was much more complicated and expensive.

this will be a roller coaster ride for you... rents at 400 to 500 a door just are.. and section 8 is in no way guaranteed you simply have not owned them long enough to understand this.. 

However it dawned on me this basic thinking and I should instead think of how to ride it through development for a larger return.

You assume the wife is gone but as with most situations like these....there is always more to the storyI would be inclined to let it ride as is for the time being and how it plays out.