*Soon after, I will be moving to the South, where I will purchase a relatively moderate-priced home (less than $350,000), likely a single-family, possibly a duplex.~ I will most likely purchase the first home (multi-family) using a bridge-DSCR loan combo or a FHA203K (3.5-20% down). 

If your target tenant is looking for a car-less lifestyle then you’re going to be competing with units close-in so you’ll have to win on price or features to get them out to 82nd.

Otherwise, walking away is likely the smarter move.

In my experience, property management companies often lead to higher vacancies, higher maintenance costs, and lower rental income compared to competent self-managing investors.

Quote from @Martin Phinney: My wife and I are considering a move from the Seattle area to the Scottsdale area to be closer to her parents.

Even competent 3rd party management can only mitigate, not necessarily address many of the issues that arise when owning lower tier properties & population growth alone is not a magic pill. 

The best strategy I seem to have deployed so far was to contact all my current tenants and let them know I’d give them a cash referral fee of $250 for anyone they recommend to me that goes through the vetting process and successfully moves in.

I know pools are a must have amenity to compete in many markets and I have to admit that I'm a bit hesitant to enter those markets due to the potential liability risk.

Then just ask: Hey, since you moved out of state I was wondering what your intentions were with this house.

4) How fast can you move if the agent brings you exactly what you are looking for?