In short I feel aimless in my research and am looking for help deciding on a direction

Shortly thereafter we stopped working with this individual, he was surprised to find out that as a customer you too can be fired by a Property Management company.  

Are you able to find long term rental properties that cash flow in Bend these days or are short term rentals a better route?

Do one short term and one long term for a year.

Good thoughts @Jay Hinrichs @Chris Seveney @Brady Durr.What about notes as a short term strategy, where I’m taking equity out of a market like San Diego, and placing it in something like notes until I’m ready to invest back into Southern California?

There is no savings by dealing with the seller's agent.That's the long answer.The short answer is YES, you should use a buyer's agent. 

But is the more conventional choice.The 3rd home is a short sale about to list for $650,000 a 3 bed house with an illegal 1 bed ADU in back yard, the ADU rents at $1200 currently and the house would prob rent for $3000. 

I’ve read online and some articles say to short sale but I wanted to see if anyone has any other opinions or can help explain some things.Thanks guys!

Weekly farmer's market, multiple LARGE cultural festivals, a sufficient music scene draw, some minor league sports arenas (Hockey, Basketball), and a flourishing LGBTQ+ community to boot.   

That's helpfulSo we bought the property less than 1 year ago if I get the note to partners name then is it considered a short-term cap gains?