I subscribe to a small lottery for one ticket, costs $4 a month. Half the proceeds from ticket sales goes towards charity and half towards running the lottery and winnings, so I look on it as if I donate $2 to charity each month and $2 to a "gambling habit". I've done this for years now and never won a dime, not even those tiny winnings, but the cost is so small I can't be arsed to quit.
As for winning, yeah I agree that it probably depends on your age. Let's see:
0-10: Buy toys, buy Toys'r'us, buy a house made of lego, hire Johnny Depp to be a pirate at your BD parties.
11-20: Hire a kickass tutor to help me get top grades in HS+College and do all the mundane stuff for me like write reports. Hire famous bands to play at my BD parites, buy a limo and go to school in style, spend RL money on in game items/gold.
21-30: Travel the world with a new girl for every trip or "fuck my way across Europe and Asia" as someone said, buy a small and good European brewery and rename the brand to something cool I decide on, buy a sports car, buy all the games on Steam, buy Steam.
31-40: Find a good girl, marry her, buy a large house with a maid, cook and someone to look after my collection of cars, enrol my kids into expensive private schools and give them home tutoring as well, make sure they have a great life, buy a yacht and vacation on it.
41-50: Hire a PI to watch over my kids and make sure the only stupid shit they do won't fuck up their lives completely, buy a sports team and rename it something silly, start banging the maid and/or the cook, set up a charity.
51-60: Divorce the wife, marry the maid and/or cook, buy a Ferrari, hang out with my sports team and get drunk on my European beer, have a mid life crisis in style.
61-70: Divorce the maid and/or cook, settle down in Florida, find a good third or fourth wife (depending on if I married both the maid and cook, or just one of them), spend lavish amounts of money on my grand children, complain.
71-80: Get that expensive and illegal organ transplant in Israel, hope to live for another 5 years, try not to piss myself, buy some Viagra, buy Phizer.
81-90: Donate a shit ton of money to geriatric research to try and find some way to make the pain stop.
91-100: Hire 24/7 well armed security guards to watch over my comatosed body so that none of those ungrateful heirs get their money by pulling the damn plug!