Seek out the smaller relationship oriented banks in your market and begin borrowing from them even if their terms are slightly less competitive than a bigger bank.

Love the style/look

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.

The other is a service and sort of hospitality-oriented approach.

In the long run, Roth-style retirement accounts beat the Traditional retirement accounts.

As well as other discounting styles (Airbnb has early bird discounting and some others).Also, consider loosing cancellation policy.Good luck!

One thing I was considering was an LLC/S-corp style entity where I can manage it while they get equity.

The 3 main banks here are BPPR, Oriental & First Bank.  

Taste and style changes more frequently in these areas, so they feel dated faster.  

When buying the house, we made the mistake of getting an inspector recommended by our realtor who seemed credible and detail-oriented but I think just wanted to get us into the house.