Good deals and Not so Good deals

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Hey all,

This is my first time posting so bear with me. I've recently decided to start investing in RE because I'm sick of paying rent but often when I read about all these good deals, the numbers I see posted on these forums are usually all really low compared to the prices you would see in a larger city. In my case I am in Chicago and it is almost next to impossible for me to find a positive cashflow property in a decent part on the Northside. Since I can only put 10% down my philosophy right now is to find a rehab condo, owner occupy for at least a year, and see what happens from there. I'm almost certain I'll lose money in the beginning but that's why I'm trying to work some sweat equity through a rehab. More importantly, I'm just trying to gain some experience in the whole process of actually making a purchase. I just want to take the plunge, I just don't want to lose all my money in the process. Right now, with 10% down, my mortgage payments on a 150k property might be around 900. Add in *** and Tax and that will bring me to around 1400.

Current rental market for a place in that location looking through online ads look like only 700-900.

Is this just a really bad idea and should I simply consider looking for another area of Chicago where the mortgage payments would be closer in line with the rents? I just can't imagine positive cash flow without putting down more money. Any body have any suggestions?