As a new investor, I am looking to find my niche and decide which lead would be the right fit for my business.

Ideally I would like to make 15 - 20k on my first flip. 

Duplex is a great idea, live in half, rent half, save money, leverage that duplex for the next property, etc.  

Plus, any parts that they would have fit into the old existing unit would just be a band aid.

There is one student who is my contact who I deal with, he is in charge of collecting rent from the others then on the day rent is due writes me a check for the full amount.

I agree with @Adrian Chu and @Alex Chin for the Seattle Market having a pool does not fit and it's better to fill it.

Ideally this would be an owner of an apartment complex that also owns smaller units, such as SFH or MFH, and trade services for these smaller properties they may not want to keep anymore.I am certain this wouldn't be easy to find but is it a good idea to find owners that fit that category and try to make a similar deal?

However, as a primary residence for me it would be ideal (my wife and I are coming back to the are from New York, and this reminds of the nicest blocks in Brooklyn, the West Village, UWS etc.).  

That kind of fits in with what @Ned Carey mentioned.  

We may partner to do this deal which would be my ideal situation since she and her husband have done many flips successfully.