I've flipped several properties in Eastwood Hills East and surrounding neighborhoods, with about half selling to homeowner occupants and the other half sold to investors with tenants already in place.That said, the specific property you're considering is key.

All state said they cover cash value for properties built prior to 1940, drewlling comes out less than half of asking price.

Maybe learn about buying a duplex and living in one half and renting the other half out called a house hack.

I suppose what I’m trying to figure out is: if my property is 1.5 - 2 miles (30+ min walk) from the closest cluster of hospitals, how much will that impact the units desirability for most nurses?

A couple options… 1) Coast as is until March for better selling season, more buyers, higher price. 2) Raise the rent at least half way to market.

He would show up, realize he didn't like the view of the water tower half a block away and back out.- Getting under contract and then reducing the price because of findings is common, but major reductions are likely to tick off the seller unless you have strong justification.

(It reminds me of a tenanant that I had difficulty with.... they always had murphy show up to mess with them)I have about 12k invested, its been long enough that they have paid back about half. 

As per verbal agreement they consider that their client and collect half of your split( in addition to the house split)...What is reasonable to be considered someones client?

We half-finished the basement, adding drywall, paint, and trim.

I didn't want the bugs to move to the other two units so I covered half of the expense and the tenant paid the rest.