She won't cash flow, but she will likely only be paying a fraction of what she would be otherwise paying for rent or to buy her own place.I also wouldn't say she has to forgo these things for the next 10-15 years, just long enough to build some equity and save up a little more money (which she'll do given the reduced housing costs that come with house-hacking).I think your main constraint is the HNI loan.

Apologies for going all over the place on this post, tried to cover as much bases as possible.

I have a former tenant that I finally got out and she sold me with a song and dance.

OR do you forgo the meeting all together because of your anxiety and just scavenge the forums here on BP?

Or if they’re a flipper, I forgo any commission for the listing. 

You hit on all points and I appreciate you for going into detail. 

@Angelo Wong when the times get tough, the tough get going as the song goes.

As for go wings, I approach them just as a realtor might with selling a home.

A loud speaker and keep playing the  "Barney " theme song .

I think there was a Stephen Stills song   " Love the one your with"