Well as a true billionaire I would choose to live in multiple areas.
My main Residence likely Lakefront Manson on the North Shore.
A double decker Pied-à-terre penthouse in one of the new Skyscrapers DT Chicago.
There is nothing I need anywhere else in the world that offers more than I want than Chicagoland.
A three month winter oceanfront get away property in SW Florida anywhere from Sanibel to Naples.
The Summer getaway, a lakefront mansion on Lake Michigan likely in the Traverse City to Petoskey areas.
Not quite sure where my forth place would be yet. But they all need to be accessed to my private jets and helicopters. Upper Michigan airports are well suited for that.
I don't desire Mountains or Deserts. Waterfronts on big waters would be what I desired most and being on the water in likely three separate boats/Yachats of different sizes so I don't have to move them.
A billionaire like Ken Griffen [1] has so many properties its crazy. I wouldn't go that nuts or build a $500 million dollar compound in Cali either. But I might consider something in Ca. Just not sure what part yet. I know the Bay Area the best but would be open to other properties south of it on the Ocean.
[1] This is before Ken bought a North Shore 58 million dollar mansion. The link is 3 years old and most of the records were broken. Not sure about NYC if that was broken.
https://www.cnbc.com/2015/10/04/ken-...ate-spree.html
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Over the last two years, Mr. Griffin, the chief executive of the investment firm Citadel, has gone on a multicity real estate shopping spree. He has spent nearly
$300 million and set new price records in three cities, according to people familiar with his buying. They requested anonymity because they were not authorized to talk about the deals.
The buying binge includes the purchase last year of two full floors of the Waldorf Astoria hotel in Chicago, the city where Citadel is based and where Mr. Griffin, 46, has his main residence. He paid $13.3 million for the 37th floor and $16 million for the 46th floor, totaling just under $30 million. If combined, the deal would be the most expensive real estate purchase in Chicago.
In New York this year, Mr. Griffin agreed to purchase three full floors — totaling over 18,000 square feet — at 220 Central Park South, the condo tower under construction in Midtown. According to people familiar with the deal, the purchase includes a main residence as well as several other apartments that could be used for staff or guests. Mr. Griffin paid around $200 million for the space — a price that brokers say is a record in New York.
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Mr. Griffin is also making waves in Miami. According to people familiar with the deal, Mr. Griffin closed last month on the penthouse of Faena House in Miami Beach for $60 million — a record for Miami
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Mr. Griffin already owns homes in Aspen, Colo., and Hawaii.
Why is Mr. Griffin spending so much on real estate?
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In court filings, Ms. Dias Griffin said that in 2014, Mr. Griffin earned an average of $100 million a month, or $68.5 million after taxes. Mr. Griffin didn't deny the claim.
So while his new real estate portfolio may sound expensive, the $290 million total still represents only about four months' work.