[trhoad]

I never really understood this. Unsure of the US, but holiday lets are notorious for being poor investments in Europe (just look at the markets in Greece and Spain). $100k buys you quite a lot of long-term lets (rentals) over the next 20 years. Why not just rent a place without the hassle of maintenance, taxes, stress, and hand back the property after a few weeks? Also your priorities and interests might change, so some flexibility on renting different places at different points (with children that grow up and also have different interests) might be appealing.

[atmosx]

You can buy an apartment in North Greece, near the sea (200-500m away) for 40k. We're talking 30-40 years old apartment, 1-3 bedrooms, etc. However, in the islands that kind of money won't get you much.

There's this app, that offers just homes in London but should offer something in GR islands soon enough... https://flyway.app/homes it's a shared ownership model, no affiliation.

[Komodai]

Wow, The idea of flyway is so interesting...