.$250/mo cash flow on $150K equity = 2% APR (not good)Find a way to boost your net income from this property or refi to take some equity out and reinvest that equity.Personally, I find it is tough to make the numbers work on small Multi-unit complexes (depends on the market).Make sure you have a good plan to manage the property and have maintenance and leasing figured out.

That is a mental game for each of us. 

A great PMC would proactively recommend increasing rent based on area comps, what upgrades to a property should be done between residents to boost that rent rate and if selling one property for 3 smaller investments would be more lucrative.A property Performa should be the baseline to return to for regular review.

Buying another property every 12 months is a great plan and also doing some value add to boost value/increase rents.

The time it takes to grind out this kind of personal financial position is a great opportunity to invest a few hundred hours in podcasts, books, videos, networking, forums, etc. to emerge with a really strong mental foundation to invest in real estate. 

Now an official ESA letter is required from a licensed mental health professional giving landlord proof that there is a legitimate need for emotional support.3.

I'd add a bit to the value mentally given that it's a bit older of a comp. 380k, but it's a floor comp not an equal comp.Second would be 15 N Preston St for me. 

This method frees up all my time and mental energy towards real estate.

Can you suggest a calculation, paradigm shift or question(s) that I can ask myself, to help me realize that a higher interest rate on a refinance would still be worth it (if the cash out is used for a good property), and help get myself over that mental hurdle?

I second what John saying and think laundry can be a nice boost especially for 4 units.