Pick their brain over coffee, and ask them discovery questions to uncover what their pains are and where someone like you could potentially help out. 

Hi Janet, If you want a true vacation home that your family can use, it sounds like you are looking for a good property to Airbnb so that you can block off dates to use yourself, correct?

What I do when looking at potential properties is to go to your location on Air Bnb and see how many similar properties there are and take note of those properties calendars to get an idea of how many of their future dates are blocked off.

Habitat also does something called "A brush with Kindness" where they might work in the surrounding blocks improving the exterior of non Habitat houses as well. 3-Trends with Housing-The family tends to stay in the house for a long time.

The numbers should be painfully clear.

@Van Hoang Indianapolis can vary block to block and even street to street.

I drove block after block of the neighborhood and the houses there are huge!

Even in rougher parts, if you are looking for neighborhoods in transition you will likely experience better returns over the long run, and you could interact with the direct neighbors to get the feel for that particular block and how the area is.

I agree with @Ryan Swan in that solar leases are a big pain.

This was the only way to do the open-concept because the wall separating the kitchen and the what was living room and what is now master bedroom was a concrete block wall.