There's a part of the fence on the side of the house that collapsed but that doesn't effect the homes livability.So, I'm terrified I'll get this under contract but won't find a renter/buyer that is willing to do the work to fix the house.

But is it as cost effective? 

For example, 4% mortgage interest rate for somebody in 28% tax bracket would be (0.04*(1-0.28)) 2.88% effective rate that would be your guaranteed return.

@Douglas KrofcheckIf you have four separate units and wanted to install a central vacuum in each, it is possible each would need to be plumbed separately {for fire code reasons} - either back to a common mechanical room or within each unit - requiring a separate canister/motor to be installed for each.While a central vacuum would be a nice perk, I doubt it would be cost effective - it would likely be cheaper to finish all the units with hard flooring (no carpets) and buy a $50 Bissell Power Force bagless vacuum for each unit.  

My effective return on my down payment ends up being about 18%.  

Investors who know how to turn a wrench and swing a hammer will make big money on distressed real estate because there will be no other way to cost effectively rehab it.

To alter a month to month rental agreement you need to give them a written notice, typically 30 days before it takes effect.

I realize this effectively reduces the sale price of the house significantly.

Since your mom will be loaning you the money, gift tax should not apply but as suggested by @Michael Le $14k of that money could be gifted tax free and not loaned effectively saving you interest on the $14k.  

Honestly, there are many faster, cheaper, and more effective ways to gain actual-useful-real-world experience.I'd be happy to answer any questions you might have about the Real Estate MBA program at UW-Madison.