First off my goal;My line of work is changing at some point at no fault of my own (finance) and what I do (which pays six figures) is the target replacement level income TO WALK AWAY FROM THE JOB. 

That could also determine his comfort level in the area and if you'll want to start there.

On a makro level David is not wrong: we have seen this very clearly the last 2 years and above all it is the housing supply that is making it difficult.

Comfort level with the RE and property management teams.

They are all the same risk/no risk level.

@Zachary Scott IMO, I believe this could be pretty subjective but I think it would depend on your comfort level and risk avoidance regarding certain things, e.g. rancher on a waterfront lagoon in terms of flooding issues, age of the home and potential termite issues resulting in structural damage, roof condition and what could be underneath of it from leaks.

The level of interest I’ve been getting on my most recent listings has surpassed even my expectations.

I have not flipped a house before but I have been noticing, similar to what you show here that, buyin/flipping house in a slightly higher price point seems to have more opportunity than entry level flips.

who knows at the time) deal and were introduced to other players during the process.Get one good deal to the table and you likely just met several people who will help springboard your business to the next level.

My first idea was to buy something small and do short-term rentals for the days I'm not using it.I've also considered buying a tri or quad-plex or even something a little larger around 5-12 units and keeping one for myself.My other option is to buy something with a walk-out basement and rent the other two levels out.