Total rents at 100% occupancy across the three are $2900 monthly.I'm thinking because the financing terms are soooo attractive that it may be worth the higher risk that comes with the high PITI?

I'm a LTR guy... but it is a pretty accept fact that short term will give you more income.  

Its going to be more about those factors than any local market factors for DSCR Lenders.The lender should have gone over the prepayment provisions more closely before closing, but assuming you likely have whats called a "stepdown" prepayment penalty shorthand called "5/4/3/2/1" - this means that you can refinance and prepay, however if done in the first year of term you will have to pay a 5% fee, second year 4%, third year 3% etc. 

The most successful Chicago investors I know are all in 3 to 4 unit properties.

Tenant screening is a challenging, but critical piece to being a successful landlord / investor.

Make sure the $400-$500/month cash flow is enough to cover unexpected costs.It wouldn't hurt to look for other refi options or consider a different loan option, which might offer better terms.

Long term podcast listener but just started reading the forums! 

You want to make sure the project is going to be profitable, especially if you are taking on short term debt. 

We are considering, if successful, purchasing an additional property/rental for grad students (hopefully less wear and tear) and what seems like a consistent rental market.

I am in the raleigh north carolina area and was curious to know if there are any highly reputable attorneys and/or agents familiar with short sales.