You can afford anything. What's your indulgence?

I think I'd try to restore/upgrade a small town. Turn it into someplace that people want to have lunch, shop, and take pictures, or move to. I have places near tourist attractions or vacation homes or private colleges in mind as models. Lake Geneva, WI, Hammondsport, NY, Wellsboro PA, Mt. Dora, Florida. See that there are trees, front porches, sidewalks and streetlights in the residential areas. There would be park space with a fountain or band stand. Speaking of park space, there would be a skateboard park close to the firehouse or medical center in case somebody got hurt. There would be a free parking garage downtown. A boulevard or a pedestrian mall. The shops and eateries would have housing on the second or third floor that the people who worked there could afford to live in. Some sort of family entertainment, such as a bowling alley, movie theater, indoor swimming pool or ice rink. An ice cream shop. A library, of course.
 
We recently got a maid, and it has been well worth it.

I am the sort of person who would NEVER ask anybody to do something I would not do myself, and while I will do housework of course, it was just soooooooooooo time consuming! So a maid has been nice so we can concentrate our home life doing other stuff.

As for my next indulgence, I always wanted a Bentley. Nothing extravagant, just a Bentley Continental GT.
 
I'm mostly not for the extravagant kind of living, but I guess some of this would seem such.

A housekeeper would be among the first things to get. It would probably mean the most to my daily life - and I wouldn't be able to handle the rest without help. I'd really need a manager for everything.
I'd get a nice property which would become (almost) self-sustaining. It would include a conservatory big enough to have exotic fruit trees and bushes. Even outdoors there would be all kinds of edible plants that are uncommon here. There would probably be enough to feed my workers too. And it would be within city limits. It's very well possible here. Use of cars could be limited.

I'm not vegan. I'd eat game (there are too many whitetails around anyway, it's a foreign species here) and then of course I'd have chickens and other poultry grown, going around old-fashioned in the garden. And plenty of fish.

I'd have all my clothes and accessories made to measure. Shoes definitely included. That's the only way to get really fitting clothes and something that isn't in fashion (cause screw the fashion). I'd probably actually have plenty of historical style clothes, or then I'd combine historical and more modern elements.
 
I think I'd try to restore/upgrade a small town. Turn it into someplace that people want to have lunch, shop, and take pictures, or move to. I have places near tourist attractions or vacation homes or private colleges in mind as models. Lake Geneva, WI, Hammondsport, NY, Wellsboro PA, Mt. Dora, Florida. See that there are trees, front porches, sidewalks and streetlights in the residential areas. There would be park space with a fountain or band stand. Speaking of park space, there would be a skateboard park close to the firehouse or medical center in case somebody got hurt. There would be a free parking garage downtown. A boulevard or a pedestrian mall. The shops and eateries would have housing on the second or third floor that the people who worked there could afford to live in. Some sort of family entertainment, such as a bowling alley, movie theater, indoor swimming pool or ice rink. An ice cream shop. A library, of course.
Mt Dora has such potential
 
A semi-secret second household containing a young "wife," and our kids...
 
I've been around long enough to know I don't want to be someone's exclusive partner. I could pay the expenses of a partner's other partner.
 
Houses in my current and future frequent travel destinations. I shouldn’t want my own private jet to use for travel 😬🤦🏻‍♀️
 
I'm mostly not for the extravagant kind of living, but I guess some of this would seem such.

A housekeeper would be among the first things to get. It would probably mean the most to my daily life - and I wouldn't be able to handle the rest without help. I'd really need a manager for everything.
I'd get a nice property which would become (almost) self-sustaining. It would include a conservatory big enough to have exotic fruit trees and bushes. Even outdoors there would be all kinds of edible plants that are uncommon here. There would probably be enough to feed my workers too. And it would be within city limits. It's very well possible here. Use of cars could be limited.

I'm not vegan. I'd eat game (there are too many whitetails around anyway, it's a foreign species here) and then of course I'd have chickens and other poultry grown, going around old-fashioned in the garden. And plenty of fish.

I'd have all my clothes and accessories made to measure. Shoes definitely included. That's the only way to get really fitting clothes and something that isn't in fashion (cause screw the fashion). I'd probably actually have plenty of historical style clothes, or then I'd combine historical and more modern elements.
Hmm. Thinking further, I think I might build an ecovillage. Permaculture utopia really. In a way that would allow me to live in it without putting too much effort that I can't do anyway. (With my health I just can't do homesteading, unfortunately.)

I'd pour money into certain fields of research that are now under researched because no company benefits from it - at least not enough and fast enough to make it happen. Like certain areas of medicine, and cocktail effects of chemicals.
 
I would buy an appropriate-sized house for me, my family, and our pets. This house would have to have a bathtub (I have chronic pain) and enough room for my ~3,000 books. An outdoor hot tub would be nice, too.
 
I would love to travel. Different cities through out the world. Taking in every city’s collectible shops and sports events.

Then into the evening, my wife and I hit the night life and/or the sex clubs. The object to meet a man my wife finds attractive. Invite him back to our hotel. And watch him fuck her!
 
I'd buy every over-inflated-price vintage Gibson and Fender in the world just for the pleasure of playing each once then giving it away to a kid learning to play (with the injunction that this thing is to be played and looked after, you're only its custodian and not its owner, not to be resold for profit).

The vintage guitar collector's market is in my view ridiculous. Same with cars, hifi etc.
 
A household manager/cleaner and a car service. Also go on Al Stewart’s uk tour , all venues
 
Open my own personal Tim Hortons coffee shop in my house. It would be run by two young, pretty ladies. One day shift. One evening. My wife and I would basically be the only regular “customers”.
 
I'd buy a huge chunk of old growth forest on southern Vancouver Island, like.... HUGE. I'd build a home in the center of it, near a river. Think Wright's Fallingwater but .. organic. I'd have a helipad and no other way in or out. I'd learn to fly a helicopter. I'd just make weird little art type things all the time.
 
I was going to say a piece of property big enough to replicate the Circuit of the Americas as my own private motorcycle track, but then someone mentioned a maid and my thoughts turned... erotic. :D
 
Open my own personal Tim Hortons coffee shop in my house. It would be run by two young, pretty ladies. One day shift. One evening. My wife and I would basically be the only regular “customers”.
No pretty young men for your wife? Or does your wife prefer ladies?
 
I'd pour money into certain fields of research that are now under researched because no company benefits from it - at least not enough and fast enough to make it happen. Like certain areas of medicine, and cocktail effects of chemicals.
Orgasm research. We definitely need more smart people working on this. I'd totally fund it.

I can't really think of anything else I'd want. I don't want to be famous. I don't need extravagance though it probably comes with being obscenely wealthy. A personal assistant does sound nice. I'm shallow enough to want one that's hot but still competent.

I also like the idea of picking random poor people and anonymously gifting them a million dollars. Surprise!
 
Okay I want a Sloth, Capybara, Kangaroo, and Elephant sanctuary. Not a zoo, but a sanctuary with as close to their wildlife habitat as possible. Eventually to expand to another part for big cats.
Honestly the first step would be acquiring between 1000 and 10,000 acres or rural wooded land.
 
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