I do not do a lot of volume, so it would take me a long time to get a good data set just based on those numbers. 

My long term rentals may be boring but they've made fantastic returns.

She can't handle a long gun. 

Right now, my best advice is to determine first your exact investment strategy (long-term appreciation?

I searched for properties that stay on the market for a long time.

Real estate is not the stock market and it's called buy & hold and not buy & sell for a reason.I did sell a few properties about 10 years ago when I learned the hard way that going into cheaper neighborhoods was not the right strategy for me, so that was basically a strategy correction and it was necessary, but also costly both in terms of dollars and time.

The tenants have paid and if someone is thinking about moving out then an extra surcharge that hits if they aren't out in time for us to turn the place for a lucrative AirBNB short term rental can help massage the move out timing.That said with MTR we do not have the cleaning costs that eat up a lot of STR gross, and its lower hassle in some ways.  

@Keith Angell What are your long term goals?

I also suggest you post your listing to "Short Term Rental Listing Advice" on Facebook and let them give you more feedback as well.  

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.