@Justin Hayden hi Justin, Id definitely agree with the general sentiment here that a multi family would be an ideal first house hack, but I also wouldnt rule out an SFR.

Agree with the sentiment expressed above.

It is also sentimental to keep it in the family but how it’s been operating is always in negative cash flows for various reasons and I want to make it back to the blessing it was intended to be for my family and not a curse so yes I plan on buy and holdddddddd lol

Misfortune happens anywhere, but don't make a business decision with sentimentality.

Personally, I am bullish long term on the market, however I do keep my eyes peeled because both on state and local levels, particularly Seattle, Tacoma and Olympia, there's always chirping from the political left about new taxes (one of which I believe just passed and will be implemented January 2020 -  WA State RE Excise Increase) and regulations on Landlords.I'm not totally against taxes, but  the general sentiment seems to be very...

@Nathan G. thanks for the advice, glad you share the same sentiment about this wholesaler.

I would agree with all of the above sentiment. 

I'd echo Jay's sentiments.  

We negotiated the price to a point it made sense, but I bought this because it was a decently cash flowing asset and had sentimental value.

However, I completely agree with your sentiment on "how can you win?"