So many people gloss over properties before truly evaluating their pro forma rent.Also, I think it's a great point about this strategy working in higher rent/gentrification areas of Chicago..it seems counterintuitive.

@Joel Bayer- I stopped using the BRRRR calculator a while ago because it doesn't handle complicated financing scenarios like this well. 

@DeBret McGee IIYour best bet is to secure a deal with creative financing, seller financing or meter lease options.

Like someone else said, your RE licensure exam is going to touch on creative financing in a very surface level way, if at all.

Let's say I am based in the US but own property overseas with a mortgage.

Set for Life by Scott Trenchhttps://a.co/d/51cIiA1Starting with the fundamentals of personal finance will help ensure you have confidence and are able to withstand the risks of real estate and also set your self up to be able to take advantages of what investment opportunities come your way2. 

I'd recommend targeting areas and property types with a high volume of sales.

This sounds like a class C property based on the numbers so thsoe are typically very high costs that you will incur.

I purchased, flipped and rented out my first property this year.

If you are financing, even higher.