As someone who's never invested in real estate before Puerto Rico is a very difficult place to start, since of how minimal public data is. 

Privacy Shield, has made it difficult for companies, including real estate firms, to transfer data across borders without risking compliance violations.

@Raghul Manoharan what's so difficult with the NARPM Calculator?

I do agree some rents versus house prices can be difficult, but being creative is key...

That's great if you got a home run deal, but the reality for your first one is to try and live for free, and then get better for HH #2, and then incrementally better for HH#3, as you progress in your investing career, you will be able to recognize those great deals, but it is much harder in the beginning since you have a huge learning curve. 

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

I have a former post and the lady has been super difficult to deal with for the simplest of things.

That's unusual and it would be very difficult to find a passive investment like that.Also direct control means I know exactly what's going on.

Here is onehttps://www.dummies.com/article/business-careers-money/caree...

go to her broker, make it super difficult to work with. go after her license, go after everything and say all you want is a release. you are a consumer. the law is pretty clear. look up procuring cause. buy a different floorplan of the same house int he same neighborhood without those addresses and you'll get around it