I would also consider talking to her broker.Also, has she provided references from BiggerPockets or Google Business?

And then the last hurdle is that driving miles between your home and your rental properties by default is considered to be like your "commute" to work, and your commute doesn't count as business miles. 

If they don't have assets or well paid employment, I would consider the offer of the payment plan.

This is assuming the way you notified the tenants of the new rent was considered legal notice in your market. 

What if I consider DSCR, would it be possible to use it?

Too bad other hosts don't consider the new expectations we're receiving not only from guests but also OTA sites.

And would this be considered "capital gains" since it's re-sold under 1-year therefore having to pay a large % of tax on the profit?

I was considering reading J Scott’s “The Book On Estimating Rehab Costs” but wasn’t sure if the information remains relevant 6 years later given how pricing has changed since then. 

and maybe change the water once or twice per year).I always consider 40% of what sales person say, matches the actual performance.

Consider different strategies like mid and short term rentals as I believe the Portland area would allow for success in both (although I have heard Portland proper is tough on STRs).Best of luck!