Milwaukee will look cheap to you, but my recommendation is to stay away from low income and high crime areas and invest in areas with better school districts, especially if you are investing for someone else, you want to make sure you are buying a quality asset that will perform well past year one.See you around!

I would turn on my heat maybe once a week, in Milwaukee, to knock off the chill, but it would stay warm for a VERY long time.

And it requires that you personally stay within IRS regulations.It is also possible to set up a self-directed IRA with checkbook control.Once you move money to a ROTH IRA you cannot move it back to a ROTH 401k. 

Many investors want to stay away from them.

There are indicators to me that Cummins is here to stay.  

There are plenty of rentals in Aurora, Naperville, and a couple in Oswego but none specifically in Montgomery that I can find.There are a couple of hotels in the area, which shows there is at least some demand for stay in the area.What are people's thoughts/experiences on this?

Staying in the lines of the wholesale space...

I assumed that staying at home would be the best option for now.

I would be very surprised if they won't allow the estate to make the payment.

The tenant would pay $75 lets say per month to not have to have a deposit, your betting on that they will stay more than 12 months.