We are from NYC, and have a modest amount of money to start with - so we’re looking to learn to swim in the shallow end with property values that are more our speed.

It seems to me that there's a hard limit on how far they can rise without tanking the entire economy given the level of public and private debt as well as the impact on financial markets. 

Otherwise you need a lender willing to lend on  a non-warrantable condo in Cook County. 

You could consider non-conventional commercial lenders.

Surety bonding protects you from all non-performances and locks in your price, so bonded contractors will make sure that their behind is covered on all worst case scenarios.

They supposedly are a non-profit org that helps provide housing for homeless which works similar to Section 8.http://www.abodeservices.org/Curious if anyone has worked with them and can share your experience?

Most likely there will be some type of public hearing and neighbors will show up.

Extemely Important Question: Am I allowed to have a non-renter living in my house that is not yet a certified rental?

When Homeaway began to restrict the ability for owners to see the guest's email address or telephone number I was worried that because I could not talk to the guest when they initially inquired (as was my procedure) I would end up having to cancel bookings because the guest might not meet my requirements (age, number in party, non-smoker, no parties, etc.)

Hey BP World,NEW TO THIS REAL ESTATE WORLD....BUT we are looking to buy a house and may not be able to get pre-qualified for mortgage due to work history with current Non-Profit (Self-Employment) not being established for over 2 years.