This will help preserve your cash longer, especially since it sounds like your grandfather has more you can buy.

If so, what should Chicago do to pay off its massive pension debt AND preserve its real estate values over the next 20 years?

You have no real advantage, other than Maybe the ability to inspect, but that's likely to put your preservation guy business at risk.  

QUESTIONS:Is there any way to preserve that tax assessment through some kind of "family" transfer?

They are to preserve income and grow it at a more conservative rate. 

However, you could try to find out who the foreclosure attorney or property preservation company is that is helping the bank with the property.

The dwelling unit shall be a single-family residence or duplex unless the dwelling unit is located on property zoned C-R, C-N, C-1, C-2 or C-3 and the property meets the following criteria: 1) within 200 feet of a TARC route, 2) within .75 miles of a public park, 3) within one mile of a National Register District or local Preservation District.

Here is the book's link: http://www.amazon.com/Shift-Estate-Agents-Tackle-Tough/dp/0071605266#reader_0071605266 Now if you focus onhelping the seller sell their home and preserve their equity dollars by selling on terms rather than for cash at a discount, you can get a win for you as the investor or agent, for the seller who is stuck, and for the buyer that has good income but needs time to get a mortgage.

Are you looking to preserve your capital?

Consequently, when a lender is notified that a foreclosure has been initiated by the HOA for unpaid assessments in a super-lien state, in most cases, the lender pays off the super-lien amount to preserve its position as the first-lien holder and stop the foreclosure.There have been instances of first mortgages being completely wiped out in an HOA super lien foreclosure when the mortgage holder neglects to pay off the super lien to halt the foreclosure.