Okay this will be a fun one for everyone...

 
What would you buy or do first if you won the big bucks?
Lump sum or payments?

 
I would (not in this order)

- shopping spree!  
- buy a condo complex in Del Mar or La Jolla and let my fave providers move in free
- finish renovations on my house then donate it to a charity that helps families needing homes
- INVEST in: property, stock and possibly buy a franchise
- get my book published (and started, LOL)
- raise my rates to 5000 per hour (hahahaha, JK free to all my returning friends)
- buy TER (hahahaha, no thanks a joke, too much work)
- book all the SD beauties a trip to Hawaii for a provider retreat

 

What about you?

then buy my own island in French Polynesia and fly my faves down for tropical vacations. I would not buy real estate in U.S. or stocks until after the bubble pops.

take the lump sum.  I would look for vehicles to invest/grow my money in.  (Tax free > Tax deferred > Taxable)  

After, I would buy some real estate. (Buy low, sell high)

Then, I would spluuurge on myself =D

I'd take the lump sum, then call you up, Goldie, for some fun!

If it is a mega jackpot, get a good attorney and try to be as incognito as possible.  The sad fact is that, like some pro athletes, people are not equipped to manage that amount of money and friends, relatives, scam artists, etc. come after them endlessly.  After about $200M in career earnings, Allen Iverson is bankrupt.  The reality is that the winners trade one set of problems for another.  But I could go for a change. Sorry, enough of a downer.

Ok, first let's note that everyone living in SD has won the geographic lottery.  Be happy for that!  Try living elsewhere and you'll see.

With a lot of money, I would upgrade the housing for several family members and cover the college education of 5-6 little ones.

I'd probably upgrade housing in SD and buy a second place on Maui.

I think real estate can still be a good investment now.

I'd splurge some, for example, a luxury sedan and a convertible.

I'd travel more than planned after upgrading my bucket list.

And, of course, I'd go to Hawaii for a week, coincidentally at the same time as Goldie and her friends

Hire a lawyer.

Invest.

Pay off all mortgages and loans.

Officiate the right person to allocate my finances to me when appropriate.

Begin backpacking the world.

Money isn't everything, and all it can do is allow me to expand my ability to help the world

hookers, strippers and automobiles

As Steve Martin once said , Sex is one of the most meaningful relationships money can buy !!! BUY , BUY, BUY !!!

having worked so f-ing hard all my life, i appreciate the bounty of money and it's value from working and sacrificing. that said, i'd endow several scholarships for advanced education, technical or otherwise. these would come with 'strings' attached.....no free lunch. and not all of them for the straight A people. after all, we're still going to need the mechanics, a/c  repairpersons, etc.  of course i would make my personal phone numbers as easy to find as Donald Trump, warren buffet and that jerk mayor in NYC.  
My parents are deceased, so those would be the only family members i'd be beholden to.  Kids and other relatives, I'm there to help, not hinder by giving them everything.  

oh yeah, then i'd continue to be true and follow my motto:  ABKTWG..always be kind to working girls
 

Assuming it was in the 10s of millions after taxes take the lump sum. Then I would:
pay off mortgages on my house and my condo
buy my daughters the homes of their choice
make sizeable donations to Paralyzed Veterans of America, Wounded Warriors, and the American Cancer Society
make donations on a case-by-case basis to local children needing special medical care
since I'm a longtime horse player, buy a quality race horse or two
increase my stock portfolio
take a trip to Pagosa Springs, CO with MammaEclipse (1 of her favorite places), and a trip wherever she wanted with Sasha/Heavenly Sweet
hobby to my heart's content, for as the old saying goes, "So many girls, so little time" lol

...might help me to pace myself.  

Some of the first things (not in any particular order):
Pay off the rest of current student loans and my brother's.
Pay off any of my mother's debts and any my maternal grandparents may have.
If possible i'm buying a MAC cosmetics store or buying some stock in it lol
Get in on some Google stock
Buy lots of gold (bars, coins etc)
Buy an nicer place (or several)
Get an on the clock (or close to it) driver
etc.