So while I feel very lucky to have had a handful of  "safe" opportunities to take action and gain insight,  I know this in no way qualifies me as an investor. 

I’m here to gain as much knowledge as possible, so please connect with me and drop some advice and strategies and do’s and don’ts!

As long as you've been living in your property as your primary for 2 years, then you won't be liable for any capital gains tax up to 500K (or half of that if unmarried).  

Managing this rental so far has been easy and it rents fast.Now the SE PDX market seems to be growing at a slower rate than it was couple of years ago and if we don't sell before next year April, I would have to pay capital gain taxes.So my question is - Should I sell this house now and avoid paying capital gain taxes and re-invest the proceeds back when the market hits a downturn or hold on it this house for the long term?

It has taught me that people suck lol which I already knew of Coarse and how people will wait in line to take advantage of you if they think you can benefit them in some way .

In equation form, if: potential return x probability of gain >> cost of investment.For example, a deal that costs 10K that is associated with a 50% change to earn $100k is a great investment!

I encourage you to ignore the naysayers like @Josh Stack said and drive forward understanding that yes, while you are taking a risk, it is a calculated risk and one based off knowledge you've gained via someone who is actively and successfully doing this type of investing. 

I'm selling my home and doing a 1031 exchange, and am filing a California Form 593-E (Real Estate Withholding -- Computation of Gain or Loss).

It will also offer nothing in terms of tax benefit. 

If the property is truly worth $36.5k, just sell it, pay off the high interest loan, pay Uncle Sam short term cap gains, and you may even have some cash left over which would be a huge win.