You are paying a very high premium to purchase perceived cash flow and have actually turned the property into a liability as opposed to a asset.Your property with rent at $1000/month is far too low for a property valued at $150K and is already negative cash flow when accounting for the artificial cash flow that you are buying with your own cash/equity.

On the maintenance side, don't forget lawn care and snow removal in the winter.

I was thinking of South Suburbs such as Oak Lawn, Burbank, Evergreen Park but I'm not as familiar with those areas so I do not know if I will have problems renting them out.

I have a 6 family deal on the table.Asking price 420k I think I could get it for 400kReal estate tax reportedly is $4000Water sewer $200 reportedlyInsurance $2700 per yrGas $600 per yrElectric $750 per yrGarbage pick up $750 per yr.Plus lawn and snow careCurrent rental income $3945After purchase projection $4200 (on low end)Cash flow on purchase would be around $1200 a month...Great neighborhood A+ and the property is in great condition...Looking for help in terms of is this a good deal... and if so what would be the best way to structure it?

What i would like to know is how increasing vacancies in a class A apts effects b and c properties.Also have to remember we are in year 10 of artificially low interest rates, and this financial engineering is INTENDED to rev the stock market and inflate asset values.And the next logical question is what happens as interest rates go up?

For the lawn mowing I would call lawn mowers in the area and get bids. 

I am getting ready to pull the trigger on a rental and was wondering if I could go for a couple months with out one (3) or should I have one in place from the onset...the property has a stable tenant in place, I do have lawn care and a HVAC person.

Pay for the ticket.... or pay a property manager to do it like the kid cutting the lawn. 

The law has kept those property taxes artificially low, regardless of how much their true real estate value increased over the past 10 years. 

Are you going to be paying for lawn care and or snow removal?