But given our high cost city and sky rocketing interest rates, early and simple analysis of any property has so far resulted in negative cash flow. 

I need to make my first move so as to avoid analysis paralysis but I don't know how to go about it.I hope to meet a mentor(s) who can help me with my vision to own numerous single and multi family rentals to create cash flow, financial freedom, and a legacy for my family.

You would want an closed end second mortgage instead of a HELOC for a long term cash use like a down payment.

Which I don't do and I still get them coming sometimes.Just be aware once operator stars  options to refinance will only be private or  commercial loans tried myself and no luck hard hide is a assisted living with people in it heard of some doing some crazy stuff but hate going illegal on things like this, ended up refi with commercial forget about cash out and such, and you are bound by appraisal as a commercial property which was in our case 25% lower then if we sold it empty as a residential home.

Are you paying cash for the property?  

I bought a 110k property in cash last March.

If it were me I'd offer her a couple of hundred dollars cash to be out asap, and screen more carefully for a better renter in the future. 

While my cash flow isn't amazing today, I'm investing in areas I think will experience appreciation and rent growth, and if rates do ever come down I'll refinance and be doing great. 

You are in TX so you have the ability to buy decent turnkey new builds in San Antonio right now, with less cash flow up front, but hopefully scalable appreciation.

I am going to build a house on it with cash and live in it.