If you won the power ball tomorrow night would you

I am frugal:

1- Re-tip my Supex through SoundSmith. Find an Audire Class A amp or two, eventually; otherwise, go to Audio Research. Buy back my beautiful KT-917 or equivalent. Keep B&K tuner. Upgrade B&W 803's with 802's. Build perfect sub box for inside my fake fireplace. Take audio design course at MIT to design crossover for such and my DM 16 based subs. Well, maybe hire consultant from MIT, instead.
2- Get rid of Supercharged S2000 and its crappy sound for supercharged Lotus Evora with whatever it takes for great sound. Add Jag XKS convertable for daily driver.  
3- Undoubtedly, but maybe just add on to house. Already have excellent acoustics, but garage could be redone into third system, maybe even with movies. A second floor would be nice. A new system in my repurchase of ex-chalet in the mountains would be on the list. 
4- NOOOOO!
5- Mostly, and I don't have to win the lottery. 

I didn't win.

I'm donating all of my gear to Goodwill,  then buying a Bose Music Wave.

Inna -- it all depends on magnitude. 
If I help a hooker $3...5k per night it's believe it or not it is help. The question is if one worth it or not and some of them really do... Easy to find too. Just ask concierge at Ritz Carlton South Beach and you'll get a tremendous choice of soon to be famous ladies blowing minds gentleman with huge dollar in the pocket.

Weather musicians servants or not, they can be booked at specific price anywhere from $200 to $fewM. I booked for my birthday 2 years ago Beka Gochiashvili who is now part of Chick Corea "Friends" and paid $1k for booking. When I first time heard Beka I was dreaming him to play for my private party and I made it happen! Bob James was almost half-way down to book...

When budget is right, I'd really book many classical pianists and believe me they are being booked for private performances more often than you think not by audiophiles though. They like to spend on equipment not on artist. 

The price is right -- call it a night.

Well, given the choice I would book hookers for the private party to hear their music, so to speak.
Sad reality regarding musicians but it's always been like that.

One one and three...  

Have a couple SAT Swedish Analogue Technologies tonearms sent out immediately. 

Then start drafting plans for a dedicated listening environment. 

I would also create a charitable trust for music education and enrichment. 

Happy Listening!