Since your rental is currently held in your personal names, transferring it to an LLC before selling could complicate the exchange.

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?

I believe some of their people are likely here on the forums and can jump in, they also had a booth and sponsorship at last years BP con so if you went you may have seen them.I came across the service because I had a client who was going to self manage, and wanted me to lease the units for him, and the property was a mixed use building with his business operating out of the ground floor. 

@Desiree Board For your mix of long-term rentals (LTRs), short-term rentals (STRs), and house flipping, an LLC is ideal for liability protection and pass-through taxation.

This setup adds an extra layer of anonymity and protection.

Then I had to open an LLC for some other investments.

Once they do so, they get access to Roku free channels & can login to any streaming service they'd like with their own login.

I'm meeting with a couple agents i was referred to through my network and am wondering what critical questions I should be asking them to understand if they are the right partners for me in this market, especially considering I will be managing this investment from the other side of the country, and what info I should be prepared to provide to them.

That will, portfolio-wide, minimize your perceived tenant flight risk, and over time you'll get to an even better cash flow spot.   

What are the biggest factors of an area when looking to buy land, what should I look for?