You will want to be careful on whether it triggers any "due on sale" clause with the lender. 

A couple days away from pulling the trigger and landing a property in Indiana, fingers crossed since it's an auction.

This is going to be lengthy, but should give you a tighter outline of 'steps' (offered in the spirit of plan it out with in season/off season as you can) to help and at minimum give you ideas of what to keep educating yourself on/ who to start talking to (get pull the trigger ready for off season in other words) (both fix & flip as well as buy & hold)1.

Our project is very unorthodox as we're working in the tiny home industry but we believe we've hedged a lot of the risk by working with the jurisdiction long before going under contract with a property.I feel like our format is off or we're not putting the information that people need front and center for them to pull the trigger on investing.

Hey Jordan, I am in a similar position with the medical bills and I too have looked into the 1st position HELOC but haven’t pulled the trigger yet so I can’t give you a straight review.  

I am aware lenders will look back at 2 years of income history and with me being fresh out of college I am afraid I won't be able to secure financing until at least 6-12 months into my job.Ideally, I can start looking for places to house hack now so I am ready to pull the trigger when I do secure a job rather than waiting to find the job and then find the place.

Get a HELOC on your primary so you can pull the trigger to buy a home when you feel the market drops. 

In this game the scary part is pulling the trigger, especially as we've been pretty conservative...

I would pull the trigger.

Independent of the paperwork, selling a mortgaged home could possibly trigger your mortgage's due-on-sale clause, causing your mortgage lender to accelerate their loan, and worse case attempt foreclosure.