@Larry Smet That's something I'm definitely thinking about - I would have to purchase in a neighborhood that I definitely want to live in and that has a reasonable commute for me to do that, so I'm keeping my options at this point. I'm not too sure which part of town I'll be looking in at this point - I have a lot of research to do still. I was reading another thread on BP about the difficulty of evictions in Cook County which definitely worries me a little bit, but I guess that just means very stringent tenant screens are a must.
@Mark Fischer thanks for the recommendation - I actually just started reading that a couple days ago! You're right, the preface was definitely pretty funny to read considering the time the book was written - he clearly didn't see the bubble burst coming. Prior to that I read The ABC's of Real Estate Investing and I really liked the ideas introduced in regards to value based on cash flow and NOI - it helped really shift my mindset from small duplex buildings to larger, multi-unit buildings, though I'm thinking I'll definitely be starting on the smaller, more manageable side.