I'm here to be an asset to the local REI industry. 

And the time it was your primary residence (tax free up to the $500K exclusion).   

Surely the mighty NY real estate industry has stakeholders with deep pockets and an army of attorneys to work on this thing, no?

Like anything when you hire a professional and thats all they do, they will be able to provide more insite in to bookkeeping and your industry that the ROI is way more than what you are paying them.  

Attend local REI networking groups and meetups and connect with people in the industry. 

However, it adds complexity with more paperwork and potential self-employment taxes on all the income.Doing it as an individual is simpler, with everything going on your personal tax return, and you might benefit from the home sale exclusion if you end up living in the property for a few years.

The area is a mining community outside of Ontario (so there is risk there because without the mine there is no industry), however there should be 16 more years of mining.

I want to begin investing with a house hack, but more generally use this position (with it specifically being in the RE industry) as a jumping-off point for a career in investing, eventually full-time. 

There are several compelling reasons why this region is becoming increasingly attractive to investors and businesses alike, and if you’re considering putting down roots—or even just exploring opportunities—this might be the perfect time.Thriving Industries and Big Business InvestmentsThe economic landscape in Louisville and Southern Indiana is robust and diverse, with several industries driving significant growth.

We're dealing with a potential character change of the income or exclusion all-together.