Also, in Chicago I see it being quite difficult to even find landlords that would be willing to allow an arbitrage situation.  

I'm an investor in NJ, mostly in North Jersey but very difficult to grab multi families, anywhere south of Monmouth county there is more inventory and have a better chance of landing something that makes sense. 

you have gained experience during the years or what is still difficult?

Looking over the spreadsheet, it seems a little difficult to compare as it seems like it takes an apples to apples comparison where it assumes that if I did not buy a say, $1.5M multifamily, I would be paying 1% of that amount in rent if I kept renting.

I check on those properties now and then on Zillow to torment myself about their current values lolBiggest misconception is that I thought it would be easier with buying out of state - far more difficult than it looks 

It's a great area, it's just difficult finding the right home

I suspect they were talking about difficult turnovers with problematic renters, bigger repairs, heavy cleaning, maybe some missing rent, and longer vacancies. 

Brrrr is difficult without getting the right “entry” on a property.

The current incentive structure makes it very difficult for an assumable mortgage to actually be a tangible tool for buyers. 

It's not difficult to find properties that meet the 1% rule, but be careful what you ask for.