This property is three hours from where I reside, complicating the direct management approach.

Primarily there are Judicial & Non Judicial foreclosures.

as an overview, NPN seem way more complicated then flipping a house for someone at my level.

very complicated, seems like you'd need a public private partnership to make it work. 

Still, I'm concerned about potential tax complications given the property's location in Maui, my residence in California, and my in-laws living in Washington.Am I overlooking anything crucial here?

@K SMy situation was a bit more complicated.  

Don't make it more complicated than it has to be.

Does this vary between force of sale provinces like Ontario and judicial foreclosure provinces like Quebec and BC?

The best way to get specific info on foreclosures is through the court system if it’s a judicial foreclosure and newspapers for non judicial statesYou can pay sites for foreclosure data as well but reality is most foreclosures today do not end up foreclosing as borrowers will file bankruptcy

Cost segregations are complicated and are best left to professionals IMO.