You can take surface roads or bike to Oak Park pretty easily from Logan or Avondale if desired.

It's not your business, and could easily be taken as an infringement on their 2nd amendment rights.

For example, if ma and pa have owned the property you are looking to purchase for the last 20 years, the property could easily be assessed far below the market value.  

The concerns about the age and condition of the building are unfounded as they are easily remediated with minimal time or capital.The issue about parking is also strange given that it is an urban neighborhood and it is quite common.

Do a few deals. then once you can easily do one deal a month , worry about checking accounts, llcs, etc.

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Problem is that even those of us who play by the rules (I pay ONLY by check, send out 1099's at year end, etc) and know the rules of employee vs contractor can easily get caught up and can get whacked hard with fines, interest, etc. 

I have purchased a smaller house for my disabled brother, which he can easily manage to rent from me, with me providing all the upkeep and maintenance on the house(which will be a rental for him).

If you buy an old turd of a property that has not been recently overhauled and updated....plumbing, electric, roof etc...not just paint and carpet....then you could easily exceed 50%.  

Someone can easily sell you a mispriced (it doesn't matter if it's intentional or their own error) property and you'll be stuck with it.