Now is not the time to “test the market” with an ambitious price to “see what happens.”

Definitely staying there for 2 years and rolling those gains into the next property. 

This allows you to test all the systems and the people involved.  

I had a tenant force me to pay for some dumb azz air quality test where she claimed my air was bad and making her sick. 

I would personally roll the dice on the rental and see where it gets me if you don't have to sell at this moment. 

In your theory, if you shave off two years of the mortgage by paying extra principal you'll have a savings of $900 ($37.50 x 24 months) at the back end of the mortgage in 28 years, so let's put that to the test. 

FI is a farce; your "number" will need to be tested against inflation so think every 12-15 years it'll be up 40-50%.

Now that I dont fly anymore  I dont think I will ever set foot in that area its just way to far to drive. and personally not a big fan of the Oregon coast  unless  its Tillamook bay to fish for Salmon and Steelhead in the rivers that feed the bay .. thats the only time we go to the coast.. my wife was born and raised on Puget Island in the Columbia river ( Cathlamet) so she wants a summer home there on the island you can get river frontage and nice sandy beach and watch the big ships roll by.. 

From my experience, one key factor here is to run a thorough cash-flow analysis.. it’s not just about the mortgage payment, but also about unexpected exepnses like repairs and long-term capital improvements.If you do decide to roll that equity into a multi-family, you’ll want to be clear on your target returns.. that way you can quickly spot a deal that’s actually profitable.

Generally they are not rolled into the loan, and it's more the level of fees (say the percentage) they charge rather than any "junk" fees or costs.