In addition, the company that they recommend we work with, Prime, helped me set up my companies and though I repeatedly asked them if there were any differences in how it was set up because I was a Canadian, I was told that the way they suggested I do it was the right way.

I haven't heard of the ability to add additional $250k primaries, but I'll have to dig in to try to learn more about that!  

Kid in college and one starting to drive   blah blah blah.I'm sure there are numerous places to cut money for sure. 

Quote from @Olga Daisel: Folks,I am a mother of 2 small kids, 3 and 5.

Hi Charles, I'm also based in Honolulu with young kids and in a similar situation to you, have also thought about buying an investment property in Japan that we could use part-time and rent out at other times.

Additional Interest...

Right now I have a kid in college and my primary income wouldn’t be any help.

Additionally, I'm hearing at meetups that this could extend to multi-fam under 4 units as well, although I haven't been able to confirm.I work exclusively with smaller investors in the multi family space and would be happy to chat more about it.

Don't kid yourself regarding flips - if you are doing flips, you are not retired.

Additionally, depreciation deductions on the multifamily property could offset a portion of your rental income, further enhancing returns.Key considerations:- Financing the multifamily: Would you go all-cash or use financing?