They came back demanding $30,000, but we knew they weren’t going to accept anything.

Really depends on what they are looking for as well as long term plans.

All things being equal, I would accept these applicants, but I would require them to pay a deposit equal to two months of rent.

Essentially gamifying the learning of real estate jargon, terms, laws, etc!

However, I probably would not upgrade it but I would rent it out LONG TERM at least until you know your long term status in Portland.  

She said she had to think about something sad to calm herself down so the camera would accept her face. 

You bought long-term rentals, so be a long-term investor. 

Make sure that they review the document with you when they are at their "peak" in terms of happiness.

While short-term rentals in areas like Kissimmee, Florida, can pay for themselves and offer lifestyle benefits, the ROI typically doesn’t match what I see from my traditional portfolio of long-term rentals in North Texas.That said, short-term rentals can still be a great choice, especially if you're drawn to the area and the opportunity to combine personal use with investment income.

Another possibility I looked into is simply leave the current SFH as is since we have long term tenant, but build ADUs on the lot.