There has got to be a really awesome AirBnB type service in here for the rich but not that rich types. All that unused property, all those traveling rich people for whom a hotel is too 'exposed'. Connect those dots people! :-)
This already exists in most elite social circles, albeit informally. A shared realtor, you happen to own a yacht slip next to someone at St. Barts, serendipitous private jet flights, etc. etc.
When everyone you know owns 3+ homes and would be able to easily cover any sort of damages that they cause people are much more willing to loan out keys and open their homes, especially when they aren't there.
I'm nowhere near that level of wealth, but I've been more than fortunate to be invited on some trips that follow this pattern. I've even heard from the horses mouth how someone literally spent two years after college traveling across the world, staying in nothing but her parent's friends' apartments/condos/houses with other socialites. You can get real deep into social psychology with this, but the social rules are different for people with such socio-economic standing. Money/assets are no longer dominant social currencies (and thus more willing to be risked)... it's more personality, looks/style, and tangential social connection.
i.e. I care a lot less that you drive a Ferrari and a lot more that you can get me into X social event through Y connection, or that you can give me good advice on popular art. Gotta keep up with the Jones' somehow, and when everyone has too much money you have to find other social signals.
I'm nowhere near that level of wealth, but I've been more than fortunate to be invited on some trips that follow this pattern.
I was fortunate to end up with a bunch of scholarships and funding to let me go to a much more expensive college than I would ever have otherwise been able to afford. Guy who lived across the hall from me was the son of a pharma exec, and I ended up learning a lot about how that stratum of society works.
And that's pretty close to it. I've known people who literally can say "oh, yeah, I don't need a hotel on that Europe trip, a friend of the family has a castle I can stay in".
We recently stayed in (what was marketed as) one of the top residential, luxury skyrise apartment blocks in Thailand. For pennies.
It was clear that it was only supposed to be for long term residents and short-term tenants airbnb/tripadvisor-rentals types were "unwelcome" (I imagine to maintain the exclusive feel of the place). They literally had signs up implying it was illegal to be a short-term renter there and, if caught, you might be refused access to facilities.
However, the apartment (and the apartment blocks) was so obviously empty of long term residents, it was sad to see such a waste of space.
The owner of our apartment was someone in Oxford who I imagined was just trying to get a little money in just to pay the service charge while waiting for his capital investment to mature.
Despite the luxury of the place, this skyrise was like a dead zone. I felt sorry for the actual residents because there was no community for them.
And to loop around to a point related to your post, it didn't make for a good holiday experience.
Actually, you can test these words of wisdom. Luxury is expensive so few get to experience it. However, in Thailand it is cheap so try it out.
One thing it will teach you is that luxury is fun for a minute, but it may not make you happy. Worth trying it first before you chase it too hard in your home country and realise what a mistake it might be to dedicate too much time in the pursuit of it.
