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.

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.  

This concept aims at addressing the challenges of what to do with defunct suburban malls and maybe even empty big-box retail store spaces that are in desirable and affordable neighborhoods.

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.

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?

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.

Just the other week I was giving a tour to a potential Canadian investor, and they were shocked at how quickly a street goes from mid/high-end to....well, not as desirable.

My answer would certainly be highly dependent on his own emotional make up, his desire to relax and travel, his willingness to delegate and outsource, etc.

There are other ways to legally raise capital, however, they have some inherent disadvantages making them considerably less desirable for what you’re trying to do.   

Choose the Right Property:When choosing a house to flip, search for properties in desirable neighborhoods that need structural or cosmetic improvements.