Being a nutrition and fitness coach, your point below is the largest component that I have seen. 

The most beautiful buildings are the ones that generate the most economic value over time. 

In today's tougher economic environment, I have recently experienced two cash calls.  

That's the largest benefit of real estate.

Now if you have say 75+ doors and the economics make sense, you could hire someone on salary to be your dedicated property manager and specify exactly how you want things done, vendors to use etc. 

Financially it only makes sense to invest remote if you have a sufficiently large economic delta between the market you live/work and Milwaukee.

Especially for things like population growth/decline, economic trends etc.And what things do you recommend checking when trying to decide whether a location is a good place to invest.

I spent my twenties in the area and have seen the economic growth.

AND THEY CAN SCREAM EASY AT THE TOP OF THEIR LUNGS IF THEY WANT.BUT GO AND CONVINCE YOUR NEAREST RELATIVE TO SELL THEIR LARGEST ASSET WITH YOU AT ONLY A 5% MARK UP AND YOU HAVE NO IDEA HOW REAL ESTATE EXCHANGES WORK. 

The influx of foreign investments explains in large part why countries like Spain and Portugal are now economically performing better than the likes of Germany and France.