Our PM is filing an appeal as well to get it reduced but we'll see how successful they'll be.I've lived in IL all my life (grew up in Southern IL and moved to Chicago area burbs for college and stayed). 

I did go to the tax assessment page which gave the house a D grade and condition of average.

Unfortunately, he had a change in his life that has tied up most of his liquid capital, but that was just an example.Bottom line is that there are plenty of folks right here on BP making a killing financing deals.

I grew up in Waukesha the first half of my life.

It's not in livable conditions.

Obviously you would like to make a profit, but what are your minimums and what types of homes and conditions of homes are you looking for? 

Then after it is in better condition, get a loan against it for $50k and buy two more.

If renting it out and downsizing can provide your parent with a higher quality of life, then I agree with option 2. is assuming the downsizing is purchasing a smaller place ?

Also the housing stock is generally in poor condition in the city, and you have the typical problems that come from low income areas like crime, drugs and violence.

The answer is that, if a house is in very poor condition, a homeowner will likely be unable to get a loan on the property; without cash, a homeowner can't compete for this type of property against an investor who does have cash.