Just subject them to appearances on “Love It or List It”
Not sure what your definition of “chump change” vs. “mega purchase” is, but a new business jet goes for about $50M these days, and a 747-800 is more like $350M. I don’t know how much this cost would change if you strip out the hundreds of seats (and seatback entertainment systems) and outfit it more like Air Force 1 (e.g. full living quarters, gold-plated conference rooms, etc.).
Find a cash strapped country and buy sovereignty over a large parcel of land with access to the sea.
If you buy a 747 and don’t want seats they don’t put seats in. They’ll arrange it any way you want.
Sounds a bit like Edison. He developed a very high quality method of record creation that you had to have your music personally approved by Edison if you wished to record one.
I think it’s fair to say that $50M is chump change in a scenario where your liquid assets number in the billions, yeah? $50M is 1% of $5B, so we’re talking about the same impact as a person with ten grand in the bank buying an Amazon Prime subscription. A fully kitted out 747 is a different story, obviously.
The whole thrust of my question starts with the assumption that the “small extravagances” purchases like houses and private jets would have been made years ago. What happens later, once you’re bored and there is, literally, nothing even *remotely *practical to spend cash on?
For my part, I’d like to create a massive, real-life video game. We already have very good laser tag technology - I’d invest as many millions as are necessary to expand its precision and functionality to the point where hyper-realism is possible. Think a combination of Ender’s Game, Laser Tag, and Smash TV. I’m not just talking point and pew pew. Vehicles, jetpacks, mechs - whatever my R&D team develops.
I’d set up a multinational league and fully fund the creation of several dozen teams. Everything would be professionally filmed and broadcast to the internet - content would include live coverage of matches but also all of the ancillary stuff that goes with any professional sport.
Arenas would be built or retrofitted wherever necessary, and they would be modern versions of the Coliseum, capable of supporting multiple biomes and scenarios.
Later it will probably turn out that I’ve been using the whole exercise as an excuse to indoctrinate and train an army of loyal soldiers using cutting-edge military tech, but that’s just what happens when you’re a billionaire.
I like this idea, in principle, but hand-picking every student sounds entirely too time consuming and tedious to me.
I’d like to buy two television networks, and make sure that they both get onto all of the “basic” deals nationwide, so that you don’t have to pay for any additional package to get my networks. One of those networks would be an OTA “free TV” network, and the second would be a twenty-four hour sports cable network, which I would dub ESBFN: the Every Sport but Football Network. Then I would buy the entire WNBA, and raise their salaries to be competitive with these overseas leagues, so that there is no further financial incentive for the players to sit out (Diana Taurasi, I’m looking at you!).
I’d also become the “money mark” for my favorite indie wrestling promotion, but I would not put their shows on my network. Instead, I would work out some sort of deal with, like, Netflix or Hulu, to make their weekly shows available via their subscription streaming service, and maybe broadcast their quarterly “supercard” shows on my OTA network, like how NWA/WCW used to do with Clash of the Champions.
Oh yeah, then I’d follow Lewis Black’s advice, and stimulate the economy in Alabama or Mississippi, by building a Big Fucking Thing™ over there. Maybe a Final Fantasy-themed amusement park…
A Porsche 959, plus a 918 as a daily driver (assuming there’s one for sale somewhere not that they’re all spoken for).
Honestly, there’s nothing super-expensive that I really want. I’d probably buy a modest flat in London and one in Manhattan (for the wife), and a four- or five-bedroom house here.
Spending a lot of money on something frivolous isn’t something that would come easily to me, but after at first thinking I had no response to this thread one popped into my mind. I’d like to get a highly skilled costume designer, someone like multiple Academy Award winner Sandy Powell, to make me several fabulous historic costumes. This was perhaps inspired by having recently watched the season premiers of Galavant (which has pretty nice costumes for a goofy comedy) and Downton Abbey back-to-back.
I’m not sure what I’d do with my costumes; I don’t actually enjoy wearing fussy or impractical clothing or going to the kinds of events where these kinds of things would be worn. Well, I guess all the charitable donations I’d be making would get me lots of invitations to fundraising balls, and I’d probably feel obligated to attend some of those. So I could be the mega rich woman who goes to charity balls in fabulous historic costumes. Maybe I’d occasionally just dress up and parade around my mansion for fun.
Nah, why buy when you can rent? I want to be able to meet with any gorgeous celebrity/model/ or completely uncelebrated woman that catches my eye, and dicker with them on how much it would cost me for them to screw me silly.
Here’s something else. Tie into every city’s surveillance system, program in my preferences as to what constitutes beauty, and retrieve all the necessary information to contact them, so I can make arrangements with them. For all I know, Sofia Vergara might cost me 5 million bucks, but some equally gorgeous but unfamous woman might cost me dinner and drinks.
Sure, and I could buy a Dodge Viper instead of a Birdcage Maserati, but that would be kind of missing the point.
A modest dream for a billionaire but: about ten years ago I owned a 1983 Porsche 911, 944, and 928, all in Guards Red. Experience taught me I picked the wrong year and wrong colors- I’d get all 1989s, as a 911 cab with the G50 trans, the 944S2 with nicer-looking turbo front end, and the 928S4.
Pffft! She’s so old that she ought to be paying you.
How about you make those arrangements for me and send me the details? 
I suspected she might be old and that “Vergara” might be code for “Viagra”.
When you buy a new personal private jet what you typically get from the aircraft manufacturer is called a “green” plane (from the color of the raw aircraft aluminum inside) which is then taken to a completion center for design and outfitting of the custom interior – a very specialized process that for a big jet can be astoundingly expensive, running into tens of millions of dollars.
Goodness. She’s 43. What a shriveled old hag, amirite?
This.
Before this thread, I honestly did not know that submarine yachts were a thing.
I mean, of course they are. Sub technology isn’t exactly cutting edge anymore, but I always associate them with the military. A submarine yacht sounds like, I dunno, a luxury tank.
I just googled “luxury tank” and apparently that’s also a thing.
I really need a few billion dollars.
Well, except that it’s not clear they actually exist. I’m always suspicious when a site shows drawings, not pictures. It appears that US Subs may actually have built a single one, which the buyer is now trying to resell for an undisclosed price. US Subs itself has an interesting web page right at the moment which claims that they “had a dispute with their Internet service provider” and are presently “rebuilding their web site” – the whole thing sounds pretty iffy. I’ll just take my nice reliable Boeing Business Jet built by a real company, thanks very much. 
OMG. Are you secretly my 9-year-old daughter? Because that’s what I’d be forced to buy with my mega billions, at threat of never ever being forgiven by her if I didn’t. :rolleyes: