It sounds like he got burned on his first SFH and that made him stay away from them.My real estate agent suggested a refinance as well, which sounds like an ideal option. 

If it's not in your name, it's not your responsibility.Now, you two get married, then that's a completely different picture, depending on how your jurisdiction handles community property.In any event, I'd suggest you find a local lender and get pre-qualified.

He suggested I first try to buy the cheap lower income condos here on Maui bc they were going for 100k (everything else is pretty much 500k).

The county suggested filling out a FOIA( Freedom of Information Act) form. 

Thanks for this suggestion.

All it typically takes though is that 3 day pay or quit as @Allan Smith suggested to let the  tenants know that the new owner isn't a push over. 

I suggest getting a few opinions from a few agents.

No ..Investors don’t pay retail bro !

Are you paying retail?

Any help, suggestions or direction would be greatly appreciated!