Gotta do that first deal - average market price to be lookin

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Hi,
I am in NW burbs of Chicago where real estate can get quite expensive...In fact to get a cheap SFH retail is high $100's atleast and goes way up. To get a multi-family is a lot more...So, i am a little confused as to how to start...i am going to some clubs for the first time this month so hopefully I will meet someone that will 'unconfuse' me....

However, i read a lot that it is good when starting out to pick a small, focused area and stick to it for the first 1 to few deals...makes sense..and this area should be close by...problem is, all places close by are reasonably expensive...

I am primarily interested in accumulating income producing properties so should I:
- stick to a somewhat local area and simply try to find a _really_ cheap deal - not sure how difficult yet
- branch out to outer counties or even into wisconsin (racine/madison) where prices may be more agreeable?

Do people that have done a lot of rental property investing find there is an ideal price point at which rents vs mortgages are good and beyond, the rent income diminishes with the increased price of the property? I am wondering from some of the posts i have read so far if i should be focusing on properties _well_ less that $150k and even less than $100k for rentals rather than go higher and maybe not see a direct ratio increase in rents....

sorry this ended up long!

thanks,
Brett