If you are new to real estate investing, then I'd suggest either starting by researching being a landlord/property owner either online or at a library or bookstore.
Scott referenced some important questions which I might paraphrase as "are you planning to self-manage your investment property or are you planning to hire a management company (which will affect the profitability of your investment)?" You might also need some assistance with determining market area rents in the specific census tract that you're planning to purchase in before you determine what you can pay for a property and still have a positive cash flow.
You might want to take a look at the following website http://www.condor.depaul.edu/~fdemissi/lawndale5.pdf for starters about information on city incentive programs that are available. There is also a federal first time homebuyer credit available right now which you can research at http://www.federalhousingtaxcredit.com.
In general I would suggest that you speak with a mortgage lender about what you'd like to do financially over the next couple of years and they might be able to help you decide which avenue (condo, owner-occupied multi-unit, or pure investment property) to select. If you need referrals to any lenders, I'd be happy to provide you with some.
Let me know if I can be of further assistance.
Broker Associate, Sudler Sotheby's International Realty
What is your risk tolerance? Are you a hands-on kind of person? These are important questions to consider.
Another important thing to note, if you're going to do section 8 you can buy multi-units for $10,000 then spend $50,000 to fix them up and get the same rents with even great profit margins.
I have numerous clients that I help do exactly the things you're asking about so if you'd like to discuss your personal situation and how I can be of assistance let me know.