Our long term goal is to purchase and move to a remote ranch and for me to be able to quit my job around 40 years old.

I would try and manage it yourself if you have the time and effort. 

I've never heard of Kin, but I too am in the market for short term rental insurance.

From there you can start to identify what you are looking for.Where do you land on the follow spectrums:Cash flow and AppreciationLong term or Short term needs (waiting for growth vs get out of my W2 now)Long term rentals, Mid term rentals, Short term rentalsBuying close to home or coast to coastSelf manage or hire a PMIf you can narrow in on those, you essentially have your buy box. 

Quote from @Zach Howard: Quote from @Jonathan Greene: If you are looking at properties in the US only on Zillow, and not seeing them in person (I know you are in Hong Kong), this is just an effort in futility because you can't underwrite single-family or small multifamily deals only online.

He had >30% vacancy despite exhausting every effort.

@Ella Marie the Pro's are you can build long term wealth, the Cons are you can lose money if you cannot properly quantify risk.

DO you want to do mid-term rental to traveling nurses?

But I see people turning long term or highly appreciated primaries in to rentals.

The "easy" answer - short term rentals where your brother participates materially in the operations - this would mean 500+ hours a year.It sounds simple from a tax planning perspective.