I'll go first:
Not sure which one...PC24/CJ4/Phenom 300....
Probably the 300 as I'm a garmin fan....would be the CJ4 if it was a garmin bird.
The PC24 short field stuff is really tempting as well....

A Stemme glider.

Aircam on floats...

A turbine helicopter...MD530 or ??

Something warbird-ish....Would love a p-38, kinda rare but having that history at risk as a personal toy seems kinda wrong.

Maybe an OV-10, or even a PC-9

Ah $2.00 for several days of fantasy.....

That is a good list.
Fun to dream!

Anything that will outrun my wife’s lawyer!!


Murray

Me:

I'm buying a nice T-Bone. To scratch that "old hot rod" itch.

Probably buying in all honesty, something in the King Air family for practical day to day use. I'm typed in the 300/350, and have a bajillion hours in them, but would give serious consideration to a 200.

Go have fun plane? I would have to go sit in all the cool old taildraggers and see what I actually fit comfortably in at 6'4"/220.

When we lived in Tasmania I worked with a guy who was a farmer on the side. He had the proverbial rich uncle pass away and leave him many millions of $$. Of course Adrian immediately disappeared from his job at the railroad and we figured that was the last we'd seen of him. But a couple weeks later he came back. He apologized profusely for being gone to wrap up his uncle's estate, but assured everyone he was glad to be back and ready to work. We all had the same question, Adrian, what did you do with all that money? He thought for a moment and then said "I needed some new tractor tyres, got those".

So if I ever come into a pot of gold I didn't earn - I hope to be like Adrian.

POWERBALL & LOTTERY:

Government imposed tax on people that are bad at math.

Free will

And Free Choice

Govt didn’t impose any of it. We voted for it.
Maybe I’m remembering it differently so please correct me.

Edit to add to post:
A Phenom 300 is a great choice and one I agree on.

Next would be a PC12 for shorter trips.

Then maybe a Gamebird and a bunch of training.
Or a floatplane….

Then a loaded CC.

Something old and simple - Aeronca Champ.
Something old and complicated - Cabin Waco
Something old and more complicated - Beech AT-11
Something old, fast, and complicated. Supermarine Spitfire. MKV or earlier.
I-26.
Something to tow the I-26.
King Air, Vision Jet, PC-12, etc. Something with high dispatch reliability I could reasonably expect to fly on <1,000 mile trips with a few friends.

And, of course, I'll keep the RV-6 and RV-10.

Everything else starts looking like a NetJets subscription, Charters, or First Class with Delta.

Best Slogan regarding the lottery??? I think it originated from the New York State lottery many years ago…

“You can’t win if you don’t play!”

1st: Citabria to start getting my tail wheel chops back into shape while I look for a…

2nd: Stearman to start getting my tail wheel and round engine chops *really* into shape while I look for a…

3rd: T-6 so I can earn my big taildragger skills

4th: Twin Beech. Taigh might actually be my first call so he can start building up the perfect one while I work up to learning to fly it. It’ll take a couple years and I figure that’s enough time to become a worthy pilot. I might just have him deliver it to Doug in Iowa so he can teach me how to fly it.

In there somewhere would likely also be a Seneca so I can have a comfy plane to start building my twin experience, flying SWMBO anywhere she wants to go.

Statistically, you can't win whether you play or not.

But I'll play this.
Beaver on amphibs.
Carbon Cub FX3.
Beech 18 with its own mechanic.
A flight instructor on call to keep me from killing myself in those three.
A really nice cabin where no one can find me.
A nice condo in, say, Bimini, where my friends and family can find me.
Netjets subscription to get me to those places with minimum hassle.
Enough land in central Indiana to put each of my kids in a house there. Big enough to call it a "compound."

Or, an alternative: If I bought a Connie, how long could I run it before burning through $375M?

About 10 years ago Powerball had hit a big landmark amount, so there was a lot of media coverage about it. There was an interview with a mathematician who said you’d be stupid not to play because nothing else offers such high reward for so little risk, and people do win.

He also said you’d be stupid to buy two tickets because the odds are so remote that doubling them makes no meaningful difference.

Powerball used to be $1, once per week.

Then it was $1, 2x per week

Then it was $2, 2x per week

Now it is $2, 3x per week

I'm not sure if I have a gambling problem, but I think the state does.

Skipper, fully restored, and I’ll certify a “Sparrowhawk like” STC.

>Or, an alternative: If I bought a Connie, how long could I run it before burning through $375M?

However long it would be it would be glorious!