I bought a condo in Norman Oklahoma 3 years ago and due to the rental market, I have struggled to get another.

I did some rough calculations and figured I should be ready to purchase in the first half of 2025.

Do this enough I guarantee you will get great info, insight, and just maybe an old timer ready to retire out who's open to seeing what they can do to make a deal work.

In general, DSCR loans will require the property to be either leased or at least "Rent Ready". 

You may want to find a good agent in the southern NH area as I'm hearing that market is prime for investment with people moving up from MA, but your other markets might be just as solid.Also, since you're already an agent, it's pretty easy to get your reciprocal license for NH or RI.

Assuming I get an appraisal of $500K, I have ~$110k (75% of appraised value minus the loan) I could tap into for equity for a HELOC.Question: What is the process for getting a HELOC?

However, an agent that has off market deals is likely flipping or wholesaling themselves so you may only get leftovers. 

House hacking our basement as our first investment, we have remodeled and redone our entire basement and now getting ready to rent out.

Get out of your comfort zone.

Contribute to HSA the maximum you can, then invest to get the best possible returns and wait.