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

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? 

As we cannot field this kind of money, we'd be waiting at least as long as it would take for the NOI to pay back the principle investment just to get the money to make the purchases (thus waiting double that amount of time before being able to make any return, after the down payment and purchase using a mortgage and that repayment).

Fees are typically very high because DSTs are relatively complex vehicles perhaps not that well suited for the uninitiated.They are a neat idea in principle, but they are very real issues underneath when you go to put things into practice.

We will probably back out just out of principle if they can't move on the extra $1600. 

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

Real Estate Principles - Thoughts?