I associate it with owning undesirable properties where people don’t really want to live.

The first agent I was able to get on the phone told me the houses I was looking at were in an undesirable area.

the end result is family businesses whether it is providing residential housing or another business other than farming no longer is viable after the property tax increase and the family business ceases at the death of the original owners.i view this as undesirable.  

If I go with option 2, I can more quickly turn my LA house hack into a cash flowing asset (but perhaps that is undesirable to have an investment property in a very anti-landlord state).My temptation is to do a debt snowball on a quadruplex.

You have to learn the desirable and undesirable parts of the city you're looking at, you have to create a whole new list of contacts for maintenance and management in that area, and much more.So, as I said in the beginning, it really comes down to your personal goals and preferences. 

If you want to stay on the south side then maybe look into Greenfield, West Allis etc - plenty of dupelxes there What do you believe makes these 2 areas undesirable,I like both areas because they’re in between Chicago and Milwaukee.

The Wealthy will be the only people who own their own home in 50 years unless they live in an undesirable place like Detroit or Cleavland or any other crappy city in the middle part of the country. 

Neighborhood factors – no repair budget can fix declining local schools, crime rates, or undesirable zoning changes. 

Avoid affordable (undesirable) properties that will typically have higher maintenance and vacancy, and buy A or B properties with less maintenance and better appreciation, which is where the real money is made.

The point about the "trailer trash" mentality is that it makes it easy to dismiss tenants as undeserving, uneducated, undesirable.