I would certainly try to rent it, even at a discounted rate, until the next school cycle. 

Offer discounts for applying in a short time period or- offer a free application fee. 

do you have the new listing discount on? 

I would attempt to negotiate with LL the scope of work required for the discount.  

Milwaukee inventory has just been so low, that even very distressed properties sell to first-time home buyers without a significant discount, so in the end it's cheaper for me to buy properties that already have a new roof, windows, kitchen, HVAC etcI appreciate that insight and it makes perfect sense.

If they are good, they don't have a problem finding work so doing your project at a deep discount makes no sense for them. 

Discount off asking is -0.3%.

If you don't know how deep the water is, you may get more than just your "feet wet".Third Lesson.Cheap and discount are not the same thing. 

I would be careful when looking at discount PMs because if they aren't making money, they likely have terrible systems in place for management. 

As best as I can tell on both sites, the algorithm looks something like this:Cheapest price>least restrictions (cancellation, # of days minimum, etc)>Premier/Super host>Review Scores>Most discounts (weekly, last minute, etc)>Regular revisions