Not just real estate, but all opportunities (in fact, I'd rather start with stock investing).Does anyone know any good starter books? 

They may look at “fair market value” or the judgment amount, no way to predict.  

Realistically the stock market, real estate and pretty much every other main form of investing will not allow you to achieve this goal

This also will give you multiple streams of income to diversify so you have real estate and the stock market, and potentially social security if its still around and you have a regular w2 job. 

We have some areas in Milwaukee that are exceptionally nice from an architectual point of view, when you look at the streets and housing stock - and happen to be in some of the lowest value ares in town - like along Sherman Blvd.I do believe that the proximity to the lake will play out at some point, but it will require a complete turnover in what currently makes the neighborhoods there, including housing stock and reputation.Every new investor wants to be the smart guy, who bought low in an up and comming neighborhood and looks like the smart guy a few short years later.

Can I offset the gains of the property with the stock losses? 

Wed all like to go back in time and buy houses or stocks when they were cheaper, but life doesnt work that way.

Price gains are leaving buyers on the sidelines as they are blocked by affordability and limited supply as new listings for the month down 6.67% from last June, chocking supply and forcing prices up as more buyers are competing over limited stock.

When’s the stock market going to “correct”?

HUGE deposits probably own stock in the bank etc.