I wish I would have seen this post a month ago. I know of a really cool three-flat in Albany Park. Anyway, I like this idea. I also like my realtor who helped by my friend do this and he's now moved after selling his three flat and making around $100K in about a year of ownership.
My realtor can help you. Message me and I'll shoot you her name and number.
I would stay out of the west side and shoot for the north side. I would try to get three units. I am warning you that you will not cash flow but you'll be paying rent to yourself. The deal my friend had with his three flat was the tenants paid the mortgage and he paid the rest, about $1,200 to live in the 2d floor 2 bedroom unit.
What is the physician loan you are talking about? You're going to want something where you can have a 3.5 or 5% down payment by living in the premises. But the banks often won't loan more than 70 or 80 LTV.
I think this is a good idea and very realistic but you're not going to live for free unless you want to buy a 4 unit in Hammond.
First thing I would do is start searching on Trulia for north side three flats. You can run a search using 3 or more bathrooms, which is often a default for units as most apartments have only one bathroom per unit. You can move the search around. I saw some nice buildings around Lincoln Square, which is a very desirable area.