Financing:  My credit is good, but again I want to clear up some personal stuff first for peace of mind. 

That just blows my mind.

Always think with the end in mind and what you truly want to achieve and take it a step at a time.Best of Luck.

I hate to get in a rush at any time and perfer to buy every single property I can in all cash others like to use other people's money because that makes sense to them and they do not mind dealing with loan and interest payments, they learn to use that to their advantage but to me that would not be an advanatage because of the way I want to live my every day life.

As you compare the city to the suburbs, keep in mind that taxes are higher in the near west suburbs, so the lower purchase prices can be deceiving.

He is one of two people applying to rent the apartment, and is a high-functioning autistic adult.

So you want to be mindful about what you are representing to the consumers (e.g. are you a luxury contractor or a value contractor, etc.). 

It’s been a tamer and mellower market this summer with houses staying on the market longer, but is really a function of price point.

I don't mind using leverage to get there but whatever you do don't be over leveraged before a crash in the economy.

Bpeace of mind, less time, less active management