If I won the lottery and suddenly had $100M (after taxes, etc.) I would:
1. First thing I would do is hire a personal assistant. There are going to be a lot of things to arrange (lawyers, realtors, employee interviews, vacations, security adviser, financial manager, charitable contributions, etc.) and having someone to handle all the hassle would let me enjoy those experiences.
2. Next I would hire employees to help me free up my time from the stuff I don't enjoy (Maid, grounds keeper, personal trainer, part-time cook).
3. I would of course make real-estate purchases for me to enjoy:
1) Nice house in Cache Valley (love that place and would spend ~$1M)
2) apartment by SLC temple for when I want to come to the city for Jazz games, flights, concerts, Christmas lights, etc. (~$2M)
3) 1,000+ acres in the mountains for hunting/fishing and to set up a nature preserve for approved public use ($5M-$20M, including a trust for maintenance).
4. At some point I would set up trust for my posterity with earnings distributed as follows:
25% reinvested in the trust.
25% available to any of my descendants for mental health counseling and student loans with interest equal to inflation (capped at some amount). Failure to repay student loans would result in loss of eligibility for descendants from the person who failed to pay.
50% to be shared equally among any of my children that are contributing to society and not bring shame on the family (no sleeping with the maid, serious crimes, etc.). After all my children have died, these earnings are included with the self-improvement portion of earnings (mental health & student loans).
5. Find a charity or cause that I can dedicate my time to. My wife last night said she would love to oversee an organization to help pregnant teens who would like to give their child for adoption. She would provide medical care, room & board, and help the girls through the adoption process. She also thought it would be important to help the girls graduate high school and place them in good jobs.
6. I wouldn't give ANY money to family, but every year I would invite the entire extended family on a nice vacation (Disney land, Beach house, Cruise, etc.). Thinking about it, I would probably offer to pay for my niece's/nephew's college (as long as they didn't do anything to piss me off like drive drunk or cheer for Lakers).
7. I would do things with the kids. Walk the Appalachian trail, sail the Mediterranean for a month on in an actual sail boat, hunt men in New Ginnea... you know, family time!