What are the legal options of landlords and property managers in this situation?

I'm wondering though, if I market them as lease option/rent to own, will a PM show the property, handle paperwork including the option contract and then manage the property or does that require a real estate agent?

You don't have to, decided to do so, because we felt like that was the safest option and to not carry the liability personally, however, it is not required. 

It can be, but they also have an annual fee option which is $499. 

Check the Chicago laws to see what your  options are as far as saying no. 

That being said I've looked into P2P lending as an option.

Can you seal the space  between the houses. offering to pay half is also an option , not sure he will take it. 

I also have the option of a purchase mortgage with a pledge of the down payment from investments but don’t have to actually put the money down, vs a conventional.

.-- A little further from you, Park County is a great option.

I'm adding now Wrap to my vocabulary of course. my next question is where can I go or with whom I can talk to explain more in deep these options, the pros, and cons, and hire someone to help me and teach me all the paperwork that I will need to do properly and make a real offer, and to try to buy without traditional bank loans a property that I want for investment.Thank you so much for your help and time