If You Won the Lotto Would You Stay in Chicago? (Aurora: foreclose, houses)

[Drover]

Not year-round but it would be my primary base of operations.

[jwaiter]

chicago summer, miami or st thomas winter

[ChiNaan]

I'm not even sure I would stay in the U.S., let alone Chicago.

[Jesse69]

LA and NYC -- too big, too crowded, too expensive, bad traffic, but a nice place to visit. I'd just packup my minivan with my Yakima Skybox 21 Pro and load it up to live temporarily there for 4 months... Enough time to see enough sightseeing and taste good food.

Then I'd visit Tokyo, Berlin, London, China, Hong Kong, Thailand, and do enough road tripping in America.

[jwaiter]

Originally Posted by Jesse69

LA and NYC -- too big, too crowded, too expensive, bad traffic, but a nice place to visit. I'd just packup my minivan with my Yakima Skybox 21 Pro and load it up to live temporarily there for 4 months... Enough time to see enough sightseeing and taste good food.

Then I'd visit Tokyo, Berlin, London, China, Hong Kong, Thailand, and do enough road tripping in America.

So we know your travel plans, but you never indicated where your home base would be located.

[marothisu]

I'd buy a new condo here, NYC, and somewhere in Europe either Italy, Paris, London, or Istanbul and probably in the caribbean like British Virgin Islands...and maybe the LA area and I'd travel all over the world for awhile.

[Attrill]

I'd stay in Chicago and also buy a lot of rental properties along the Blue Line to get some return on the winnings. I'd probably also buy a place in London and a place in Tokyo for vacations as well.

[Jesse69]

Originally Posted by jwaiter

So we know your travel plans, but you never indicated where your home base would be located.

My current Wicker Park home is home base. Large enough for my $35,000 collection of bikes + $45,000 of women's clothes too. Now if I had a wife + 2 kids I'd need a 2nd house. I don't know my plans for that.

[andrew61]

Originally Posted by Jesse69

If you won a $100 million cash value lotto, would you stay in Chicago or move to a better place?

I think I'd buy a penthouse in Chicago and live here part-time, but I'd have homes in other places, too. Maybe a pied-a-terre in NYC, another in Paris, another in Buenos Aires... I'm still working on my list of places in the world I might like to live. And I'd do a lot of traveling too.

[emathias]

I live on the top (4th) floor of a vintage building. If I had 100 million dollars, I'd buy the place across the hall from me and the the other unit in the building with a single parking space and the unit below the guy across the hall (because it's always filled with college kid renters) which would mean that I owned the three single spaces next to the building. Then I'd integrate my place with the place across the hall and turn one of my three parking spaces into an elevator. Then I'd add a penthouse level to the integrated places with a killer deck. The third-floor unit I bought to kick out the kids I'd turn into my office to run my investments. And the other unit I bought just for the parking space I'd strip of the space and resell to someone without the space.

The two other parking spaces I'd dig down below to create a wine celler, and over that turn the spaces sideways to better accomodate large cars, with them stacked like you see in Manhattan sometimes.

That'd leave me with about 3,500 square feet of top-floor living with and elevator, two large parking spaces, a wine celler and a killer outdoor space and a very large office. All it, that'd probably cost me about $2,000,000 to do.

I'd also buy homes in New York, Paris, Shanghai, Norway and maybe somewhere else, but I can't see making anywhere else my primary base.