Trying to understand the risks involved with cash out refinancing

[A.J. Zunino]

Hi community! I am a first time investor and am researching and learning as much as possible before I take the plunge. My partner and I are planning to begin on making offers starting Summer 2025. I have zeroed in on a few markets (geographically and type of renter I want to cater to). However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line. My strategy is BRRRR.

The way I see it is: I purchase a property and rent it out to hopefully breaking even on the mortgage. The goal is to cash flow so I will rehab the property and increase the rent. My property value will appreciate from my rehab and also with the market. 

Here's where I struggle to comprehend and make it make sense: So when I go to cash out refinance, the property is appraised at a higher value from market appreciation and rehab. When I complete a cash out and refinance will the new mortgage be higher? And if so, how do I keep the property cash flowing / in the green? 

What am I missing here? If this is how a cash out refinance works, it feels like the strategy is to either have more to rent out within the property (multi-family), wait for average rents in market to increase, rehab the property more and increase rent more, pay off the property/ more of the mortgage and refinance again without a cash out to decrease the mortgage (I don't even know if I can refinance a property twice)? 

I could very well be looking at this wrong. I am reaching out the community to ask for help and advice. All thoughts, critique, and stories are welcomed and encouraged!!! Thanks.