Chicago is so vast and diverse that 400k can get you a tiny condo in one neighborhood and a 12 unit in another. 

I also come from a project management background, so was well aware of the amazing feats that can be accomplished with a competent team.When it was time to invest, I scanned all markets I had any sort of access to, evaluated which other ones I could enter with reasonable safety by utilizing unfamiliar teams on the ground, then crossed that over with potential returns.I'm a pure cashflow investor, never like to speculate, so reliable monthly cashflow was criteria no. 1, followed closely by no. 2 - ease of management and low maintenance, then finally no. 3 - Affordability (which equals hedge and diversity), and last but not least, no. 4 - would I like to visit once or twice a year, at worst case, if things require my hands-on attendance.A combination of the four pointed at Japan, which is where I'm primarily invested (with smaller portions of our family portfolio in the US, Europe and Australia), although I'm only living there half the year at this point, thanks to good team utilization which means I don't need to go there unless I want to - this may change now that the yen's down and our son's nearing primary school age - which is the whole point of renting where you live and investing where the money and the environment works for you - to retain the flexibility and lifestyle benefits of being able to work and live anywhere we want at any given time.This is, of course, a long process of rationalization and calculation summarized in a nutshell - if I haven't bored you to death yet, and you want to hear more about the hows and whys of investing overseas, feel free to contact me. :)Best of luck in your chosen path, you seem to be considering all the right factors before embarking on it - I'm sure you'll enjoy the ride.

Real estate is such a fun and diverse industry.

There are definitely people doing well here in Chicago though, and I don't think you are going to find many markets that provide the diversity of opportunity that exits here.

Looking forward for discussions and learning from your experiencesJohnny AlvarezIn my opinion, Chicago's too diverse to answer the question- "What's  the best neighborhoods to house hack?"

MN is actually wildly diverse, we have 4 distinctively different geography regions in state.

It’s closer to downtown with a 10 minute light rail ride, is right off the freeway, and more walkable, more diverse, and better cashflow than Ravenna and most of north seattle. 2 of our 5 properties are there and we LOVE the neighborhood. 

I have never been to Chicago but from what I hear it is very diverse and a hero wing population.Since I was born and raised in Dallas I know there are plenty of options around there.

North Eastern Pennsylvania is a very interesting place for real estate investment due to the diverse market and wide price swinges for inventory both in the acquiring and selling aspects. 

As a member of the Wisconsin Realtor’s Association, I joined the cultural diversity committee after reading “the Color of Law.”