Ideally AI could improve the property analytics that shape listing prices, a competitive advantage over other brokers.

Investors are almost always the biggest challenge for any group, new or seasoned, but especially newer investors.  

Welcome to BP - house hacking / mid term rentals are great strategies esp starting out, I think you are right on with initial gameplan (Oregon can be challenging for landlords though so good that you are open to other markets)

Property value is land + improvements (the structure). 

The if is the challenge as ground up ADUs typically cost more. 

A licensed property manager should have access to the MLS which would put you on realtor.com, Zillow, and probably a dozen or more other websites.You don't need professional photographs, but they should be improved.

This price range makes cash flow neutrality challenging, especially in desirable areas like beach or lakefront properties.

Challenges?

I started investing locally and have kept expanding after moving out of state, so I’ve got experience navigating the challenges that come with investing from a distance too.Detroit has its challenges but also some of the best potential for cash flow combined with affordable entry points.

Challenges?