So she would have earned say 5% on her $280k (from a traditional sale after commissions.)  

You can always sale on your date and convert appreciation to monthly cashflow.  

I dont want to get a loan for more than the true sales value of the property but I would like to get atleast the normal amount back for the money I have put into it. 

In general, most people value STRs for sale based on the income of the STR.

Check out Zeona's book 30-Day Stay on sale THIS WEEKEND for Black Friday.

  - Expectations: At any given time along the entire Oregon Coast there are roughly 125+/- worthwhile STR eligible properties listed for sale.

One strategy is to pursue properties (in your preferred markets) that have been listed for sale for over 90 days (even longer is better).

Your new ARV(after repair value) should be supported by an adequate amount of comparable sales in the area(duplex's).

I was recently exploring a two-story commercial building for sale on a corner in a growing downtown area.

I see a lot of 250-300k 3/2 for sale that are going to compete with the new builds, and that size is only renting for 1800-1900 to month max, so I find that the numbers don't work for me, or are very marginal at best.