You could get a p.o.ed tenant that has to be evicted, and wrecks the place before you get them out.

This is like watching a very slow train wreck...Isn't it Rahm's job to kind of prevent this?

Actually, I had more problems when the property was being managed by a 3rd party property management company (won't mention any names here) - but essentially they didn't get a security deposit and those tenants wrecked the place and half stopped paying rent so I had to evict them - not fun.  

Speaking as an investor that invests out of my living area, a bad team / team member can wreck your investment and cause you undue financial stress.

Took some notes:Gutter - front and back had small section hanging off.Roof - good conditionSiding - good conditionFront Patio - Needs paint, is wood deck built over concrete stepsBack Fence, Side Fence - Chain link with sections brokenTree stumps - 3 eventually need removalside window - taped over crack needs replacement (I don't think repair is possible on this)Bottom windows (2) new suggests they were broken 1 is sealed over with plywood&paintedThere is more, the basement carpet is wrecked.

Post Great Fire and up to WWII, lots of 2-8 unit walkups and mixed-use properties were built, but there's never been any economic incentive to later wreck and redevelop them, so they stick around.

I'm making a good income, but it still feels like the rat race, and I've still got that itch.I went and looked at a wreck of a house in a town I don't know at all just two days ago, and I plan on making an offer on it this morning.

We would need to replace central a/c and furnaces in each unit.The units interior is not a complete train wreck, but we would have to rehab bathrooms, kitchens, new paint, flooring etc.

This year when the annual inspection came, I told her I will not fix all those things to pass, this year her boys got older and wrecked most of the house.  

Will you wreck your car if you drive long enough?