Or you could go full time, bet on yourself and make 10x that

It is up to you if you want to bet on an appreciation play and take the small losses each month with the ultimate goal of refinancing when rates fall and getting to a point where you can cash flow.

@Robert Dunbar Your best bet is probably speaking with local brokers to get a sense of the ARV.A cash-out refinance may be possible, but as @Jack Mawer pointed out, most lenders like to see some seasoning, and seasoning requirements will vary across lenders.

I bet most of the "sell and get out" crowd doesnt play in CA let alone SD. 

I want to see if he is maybe interested in getting a physical asset as well.

You make no mention of any cash flow numbers, but I bet you think you are actually getting good cash flow because you have no debt...and you'd be wrong. 

or does she need to physically ask for that or is it assumed since I know she wants it and can't get it?

Were I a gambling man, and could find somebody to take me up, I'd bet on another extension.I doubt I could find anybody to bet the other way though, so it's probably just as well I'm not a gambling man.

I bet there are people in your area who house hack by renting a portion of their primary residence to help pay the mortgage! 

Money is tightening up anywhere (I read something about bonds being pretty lucrative right now, safer bet).