I think TN forgot these people are coined "Digital Nomads" for a reason, there nomadic as in readily relocate.

I think this is the reality for those who are not willing to completely relocate.

When investing OOS, consider targeting markets with major corporate relocations and expansions.

Mainly, what % of that $500k are you able to save and is there a desire to relocate?

I've relocated to Spain and am very excited about rehab projects and a rental portfolio.

Insurance companies don't relocate the clients. 

My job is our sole income and I get relocated for projects frequently so any property would have to be managed remotely (willing to invest anywhere in the states).Given the our situation above and our long term goals, I feel best next steps would be a heavy emphasis on networking and deal analysis.

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.

Are they worth digging up and relocating?

My channel is a lead-funnel for relocation clients, usually executives.