My question is, do I just not touch the first property, use the cash flow to reinvest and pay down the mortgage or save up for a downpayment down the road OR do I pull cash out of the first property to buy the next property?

A hybrid approach could work best: start with a cash-flowing Texas rental while saving for a Long Island house hack later.

In the long run it would save you $. 

Video walkthroughs and establishing a trusted boots on the ground are just as good plus save me hours and hours of driving!

you may have to save up until you have enough money to do so - down payment, closing costs, reserves, etc.House Hacking: What Is It, How to Start, and Strategies for Successit's a more powerful way to get started. 

Eliminate debt, establish a budget, and save.

Opt 1) utilizing our savings in the brokerage account and emergency fund and pay for it all up front. 

Do I wait another year to save more, or do I look into a HELOC or a VA cash-out refinance? 

@Franklin PerezGetting your real estate license can be a smart move if you want MLS access, networking opportunities, and savings on commissions, but it comes with costs and disclosure requirements.

A hybrid approach could also work—perhaps using a HELOC for reserves while saving the stock portfolio and 401k loan as backup options for future opportunities.