But if your $15K rehab estimate is anywhere close, it doesn't sound too bad. 

I would also say that your investment strategy will be influenced by the market in which you invest.

Sell as  it is a bad choice as a rental based on rent to value.

I know people think it is courteous to give your employer several months to find a replacement, but most employers would let an employee go with a days notice and not feel bad at all about it.

My father owns 3 town house units in Hazel Crest, IL and he has had pretty bad tenants and he constantly is fixing something they broke by himself.

The sister is just willing to place someone in the house RENT FREE just for the sake of someone being there since the property is a hour and a half away.Is there a way to remove the sister out of the picture without stepping on toes too bad? 

I've made a lot of really bad decisions.

Either way the process isn't too bad, best of luck.

I don't want to do that because it would be bad for resale.I know there are those split systems, but those seem pretty spendy. 

When the furnace is bad and the roof needs to be replaced then the house can't be purchased by "normal" people who need a "normal" loan.