I’m wondering if anyone would be willing to help me out with the transaction to make sure I’m not overlooking anything and making mistakes.  

It is super straightforward and prompts me to tag all of my transactions with categories that correlate directly to Schedule E.

The information required to select an investment location that enables financial freedom is readily available and straightforward.

I am wondering if this area is 1) investable, 2) safe, 3) What is the long term outlook for this community? 

The easiest and straight forward option would be, as you said, to sell the current residence, payoff the HELOC (or most of it) and then get back to saving with your jobs and the rental cashflow.

You know, I’ve had a few moments where I’ve scratched my head wondering if I was getting too cozy with my home equity, but pulling out those funds for a strategic investemnt has, more often than not, led me to some pretty sweet opportunities.

I’m wondering if $23k of my own liquidated funds is reasonable to start looking for an investment property?

Just wondering how you feel about the unique challenges NOLA has relative to economy & climate change (insurance), population decline.  

The conversation, as well as this decision, left me wondering how many insureds are denied policy coverage and cannot afford to bring a suit against the insurer and are unable to recover their loss.

Basically I'm wondering if we should start our own LLC (owning it ourselves, "hiring" out the construction to his other LLC to avoid layering), or can I have his company get the loan and I just sign something showing that I'm providing the cash, am on the hook for the loan, etc?