Part of the motivation is to secure residency in multiple countries, have my investments in multiple currencies, and to set up an offshore structure for my company in one of these locations. 

Market risk, currency risk, inflation rick, etc. 

I recently got back from vacation and I feel like the rental car game paired with ubering around could be less of a hassle if this was provided as an option for guests.

This devalues the currency because of basic supply and demand, the printing of new currency units decreases the value of the existing currency units assuming the velocity of money exchanging hands stays consistent.  

They showed us financials bringing in over 20k a month between the pair of them....

It's too small to make it into a duplex.I know that there are small families and couples that might want an arrangement like this, but I'm wondering about other peoples' experiences with pairing together roommates who don't know each other.

If you can use the weight of your loan paired with deposits, this may sway the needle.

I purchased the BiggerPockets 90-day Intention Journal and they paired me with 4 other people.  

Currently I have zero debt and have enough liquidity to lock down a pair of SFH rentals this year.

So, you purchase price and your costs are low and, on top of that, expressed in a depreciated currency while your revenus are high and, on top of that, expressed in an appreciating currency.If you look at the risks, what I just mentioned gives you a huge margin of safety.