They got Jared a policy that ran around $4,100 a year, which wasn’t exactly pocket change, but it felt like a workable number once he factored in the premium he could charge per night.

If it's above 700 or 720, I wouldn't worry about it too much (though credit scores are dynamic and change over time, especially with RE developers).

Something to keep in mind is the lending options change when in LLC, so leverage owner occupied loans for Refi/HElOC etc go away once you move out.  

It can be tough to make money with high leverage, especially if market conditions change.

My main concern about actual house hacking for a few years in a row is that we don't want the kiddos to have to change schools once we relocate up there.I'm thinking about getting an appreciation-oriented duplex/triplex in a pricier market with good schools that we could stay in for several years, and saving for an actual cashflow property that'd we buy as an investment property instead of a house hack.

Look at the overall numbers if you were to hold something 10 years and that will change your mind real quick. 

Cost to List + Changes to Listing.Can range from $100-$400 for the exact same listing on the MLS.

Do I need to have them sign a new lease with my company name on it not changing any of the terms or do I just inform them on how to pay the rent? 

The insurance would not be valid for two reasons:1) the insured “individual” is no longer the owner2) the insurance was for an owner occupant, not a rentalMost people DO change the insurance to reflect the llc as owner and as a rental.

What if you pick the wrong project, or the wrong sponsor, or the economy changes, or the business plan doesn't work out.