This way your owner-occupied property will (ideally) be paid by your tenants and you get to live rent free!

its well known that CA transplants to Oregon and Washington is been a huge driver ( I am one )  but that has slowed a lot since the rise of values in Oregon and Wa. 

Milwaukee is a great place to invest as I am a transplant to the area from Chicago several years ago now. 

That said, you can live REALLY close to the water for $500K in the size you're talking about, and those homes make much more profitable STRs (generally) because the rents aren't that much less a block or two from the water but the price is WAYYYY less.  

My tenant will live rent-free, and I will invest further.  

Columbus is an extremely friendly city (I'm a transplant from Cincinnati for 20 years now). 

What you should probably do is explain it to her, not as if she's going to be investing with you, but, explain it to her as such - For our first few homes, we will purchase a 2-4 family property and live there, while having the other families pay us to live with us, which in turn, will probably allow us to live rent free and possibly have a profit each month that will allow us to save even more money.

NH Governor is not allowing evictions during the state of emergency, which means tenants can live rent free.

I will rent it out within the next couple months and transplant myself elsewhere for about 5 months, then seek out my next live-in investment property.

Get the skill, avoid debt as much as possible, buy the house hack and live rent free, and work like crazy in a field that actually pays good money.