Happy to get more granular if I know more details.

Have had an Airbnb out of our primary residence basement for 2.5 years and bought a duplex in November after taking out a HELOC on our primary to use for the down payment and some renovations. 

There are other, more ambitious, risky, and difficult, ways you could achieve the same end goal.

My biggest struggle right now is understanding whether to get a HELOC on my primary home or do a cash out refinance so I can get started.

For running numbers have your realtor if he invests run through it with you or use one of the free investor calculators on BP. 

I work in engagement marketing and deal with construction tradesmen all day, usually more custom type tradespersons with a lot of care and concern for their own work, which may glamorize it more than I realize.

Then $10,000 more at time of trial.  

Many have zero experience with the community and don't understand the culture.

When I used to be a Realtor, I ran comps manually using a simple spreadsheet I built. 

During the tour, we will guide you through several key areas where we actively invest and showcase a selection of available properties—many of which are off-market opportunities.Courtney, who leads my investment team, can assist you further.