While I am unfamiliar with the markets in the other neighborhoods you mentioned, I have looked into West Hill and it was something I decided against as I personally did not get the feeling of "hey, I want to live here" due to what seems to be chronic property neglect by other owners in the area.

Still get chronic complainers and threats.

The local market, he said, is outpacing the mid-2000s housing boom.With the exception of a few urban markets, including Manhattan and San Francisco, the U.S. is seeing “a chronic shortage of inventory, heavy sales volume and prices rising at levels wildly ahead of income growth,” said Jonathan Miller of New York-based Miller Samuel Real Estate Appraisers and Consultants.

Perfect for BRRRR.Now Milwaukee is dealing with a chronic housing shortage, extremely low inventory and with that even very dated houses will not get a meaningful discount.

The only material recourse in a situation where a tenant is chronically late but ignores late fees is to non-renew their lease when it expires and take the late fees out of the security deposit (but this also can get sticky if there is damage to the property, and the cost of repairs exceeds the deposit.)

Will you get your rent payment or will they pay the 2 car payments and buy food and take Jack or Jill to the doctor because of the chronic bronchitis they have had since they were 2 years old......???

I have a section 8 tenant who is just chronically bad with managing his life.

Are those super cheap properties in ghetto areas with chronic perpetual poverty?  

I'm a therapist, and one of my first interactions was with a home owner with chronic mental health concerns, so I found it fun and interesting, but I'm not sure everyone would feel the same way. 

Another great person wiped out by a chronic drunk driver allowed to keep their license.