I’m a real estate broker on the north side of 14 years and refer all my people to Ofenloch Mechanical.

I work as a Mechanical Engineer.

So even if it "looks" like it doesn't need much work it probably still does......So I'd almost always rather buy something that needs updating since the mechanical systems are almost always old anyway.

As a tenant I’d personally take more pride in having a steady funded auto-withdrawal for my monthly rental rather than getting dragged to court as if I got nothing better to do with my life.

Try Chris @ CRD Mechanical - Tell him Dana Carberry referred you - Best of Luck - Dana

Or should this fall on tenant 1 or tenant 2's rental/auto insurance? 

I studied for my bachelor's in mechanical engineering and graduated fall of 2016.

Mechanicals look good.

But when I say full gut and rehab I'm talking: taring everything down to the studs, updating plumbing and electrical throughout, probably upgrading the panel, adding duct work for heating and cooling, new mechanicals (boiler, A/C, etc) , hardwood floors, new kitchen, new dry wall and insulation, paint, finish work, etc.

I currently run a mobile auto detailing company with my wife that I started back in 07.