They currently sell attached duplex/triplex/quadplex in Central Oregon at prices LOWER than MOST resale closings on MLS.

You may be lured in by a cheap price or a pushy agent trying to sell you on a deal. 

I was referring to when you sell it.

In other words, I see the short term value in niche, but I would never want to become so niche that if I wanted to sell in 10 years I might be pigeon holing myself

Can I sell a property in one state and then do the 1031 transfer to a bigger property in another state withing the 45 day window, or does the transfer have to stay within the same state?

The only exit strategies I see is only STR, sell, or go through reserves until vacations would pick back up.While in a more metro area you can convert to MTR or LTR if need be.

If the higher insurance rates are a concern for you I suggest staying away from the high rises for now.We are surrounded by multiple military bases so there is always someone buying, selling or looking for rentals in our area and surrounding areas.

When I was in high school we have a Business class, an automotive shop and even a building trades program where the class would divide into AM and PM groups where land would be bought and entitled then they under the supervision of an incredible teacher named Gene would build a home and sell it after completion.

I have worked with owners trying to sell or purchase multi-family properties and those types of agreements transfer with the property.

The owner, who I happen to know and have thought about approaching about selling, has terminal cancer and has about 20 units altogether that he wants to dispose of.