My business partner lives in the Minneapolis area so we were thinking about getting into short term rental properties in the Dells/Lake Delton area (pretty close to a middle ground area). 

Building my portfolio May stagnate as a result if break even or negative cash flow properties keep eating into monthly expenses.I’m thinking that a middle ground between enough cash flow to cover unforeseen circumstances ($300-$500?)

My plans are to ground myself locally and next year look to begin virtual wholesaling the MD market so that when I relocate I will have already established some familiarity with the MD market, and have established few key business connections.

There have been more poor quality guests in surrounding units, maintenance of the grounds and amenities has been slacking, yet management just bought new souped up golf carts… The resort is getting bad reviews on Google for poor service (the staff IS rude, even to me before), and the resort staff is not addressing those review online like they used to.

Whether you're one block away rather than two blocks away won't make much of a difference and won't justify a significant premium.If you want to go ahead, having your parents on the ground is definite a positive if they can help with the management.

Ground was already saturated and this NorEaaster simple pushed your system to the limit. 

. $70k total: Build an in-ground pool for 50-60k, add a nice deck & outdoor tiki area etc.

Lot of ground to cover surrounding Downtown, military bases, universities, and attractions such as Sea World, Six Flags & shopping malls.

If tenants are thin on the ground in your area, I'd try to contact his former landlord and his former roommate, if possible.  

I am, like you, trying to streamline my book keeping and I am very grateful to you for bringing this topic to the table.