The new design takes the home from a 3 bed, 2 bath to a 4 bed, 3 bath, 2,400 sq ft rambler on a large lot in highly desired area.

Class A apartments have numerous amenities, professional management, and sit in desirable neighborhoods.

I don't necessary want to quit my job but having the option to do so is desired.

Which is why I pay more, for less cash flow in highly desirable areas.In high income areas, rent is a lower proportion of income so therefore your tenants have a higher capacity for paying higher rent because rent is less than 20% or even 10% of their income.

We were especially thrilled to start our investing journey with a duplex, and it was even better that the tenants desired to stay and had been consistent with rent for many many years.

So I get your hesitation to be too demanding and your desire for the problems to go away as fast as they can, however since you have NO property manager ( I don't use one either), it is incumbent that you take a more ACTIVE approach with management of your property.Let's review your situation.  1st time leak occurred, you sent a plumber over to find the problem.  

I get the desire to own outside of Chicago proper, but instead of going to another state altogether, why not invest in one of the burbs?

Second link is a similar size, albeit 10 year older home, in Setagaya Ward (a very desirable neighborhood), but still "only $1.2M. https://www.homes.co.jp/kodate...https://www.homes.co.jp/kodate...(2) Age. 

For example, my client just closed a 3/2 single family house for $160k that was already rented at $1900/month and near turnkey and in a super desirable residential area.

Playing sports isn't forever and I know a 9-5 isn't for me, I am very much desiring to get ahead and learn how to build wealth from all those smarter than me!