However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line.

Hey, I'm a house hacker myself. 1 SFH, now rented out completely, and currently in a duplex that I just refinanced. 

I also don't want refinancing risk, so any deals with only 3 to 5 year debt are out for me.

With that capital, I’m planning to either dive into a larger multifamily project in Detroit or grab a small duplex or quad in San Francisco.To reach that $500k mark, I’m leaning on the power of cash-out refinancing.

Sounds like they could have different PPP or fees that go along with refinancing with a different lender. 

If the rent stabilizes, I can then consider refinancing these properties using DSCR or other valid options (please educate me, and let me know what other options you think are valid).

Hi John,I am currently in the process of refinancing into a DSCR loan.

Im towards the end of my renovation and beginning to finalize my numbers...looking towards refinancing my loan with the new house value. 

I think you have to ask yourself what you're trying to achieve by refinancing at this point.

However, if I purchased at today’s rates (or cash out refinanced it at high LTV), it would still be negative cash flow.