As stated, this is a (mostly) detailed plan of what I would do if I won a truly massive jackpot in the lottery. This is assuming a post-tax win of $500m for this scenario, and the plan can adjust up or down based on the size of the jackpot.

I borrowed this formatting style from u/yoloyodo22 so this is their shout out.

Prior To Claiming :

• Upon discovering I have won the lottery, and after the understandable freakout and hyperventilation that is sure to happen, I will first contact my best friend and tell her that we won. We have talked somewhat extensively about this, and we are both in agreement about the ideas I am presenting. Of note, this list, when it comes to personal things, only reflects my plans. I know hers, but I am not going to discuss them, as they are hers.
• During the next available business day, we will get a half-dozen photocopies of the winning ticket, then find a bank with a safety deposit box and place the winning ticket in there to keep it secure.
• We will next consult with an Estate Lawyer that specializes in Ultra High Net Worth Individuals to find the best way to claim and utilize the winnings in such a way as to simultaneously shield my identity from the public and to make it so my wealth can still be used for good works beyond my death. This will involve forming a trust and a foundation.
• The trust will invest the wins in solid ventures. I'm not looking for massive gains as much as consistent returns, but massive gains are also appreciated for my plans. Any capital gains will be reinvested to grow the funds.
• The trust will have two beneficiaries: Myself and my friend (15%) and the Foundation (85%)
• The Foundation will never have our names associated with it. The purpose is to help others, not to create a public legacy for ourselves.

Home :

• My idea of a nice home will be to buy between 100 and 500 acres of wooded land with a lake completely contained within the borders (so it's private and totally owned by myself). On this land, I will build a 4 bedroom home with a 3-car garage situated 100-200 yards from the lakefront itself.
• The property will be left largely undeveloped and be far enough out so I can see the stars at night.
• Non-meat foodstuffs will mostly be locally sourced from farmer's markets and the like, with the occasional trip to larger markets and stores for more esoteric items.
• Meat will be sourced from local ranchers, farmers, and hunters, with me paying them for beef, pork, chicken, turkey, venison, and the like.
• The lake will be stocked with a variety of fish, ranging from catfish to bass, to provide an additional source of protein.
• The exterior will look indistinguishable from other homes, featuring both log cabin and brick home aesthetics, with the only visible hint as to the reality being the Rolladen shutters on the windows and doors.
• There will be a covered front porch and a back deck (facing the lake), and the deck will be partly covered and have an outdoor kitchen area, featuring a full grill and sink area, with both water and gas piped to it.
• There will be a lakeside patio to relax as well as a fire pit down on the ground level between the house and the lakeside patio.
• The interior will feature an eclectic mix of industrial, art deco, and retro-futuristic styles, using an interior designer to make sure everything flows properly.
• The furniture will all be custom made to be sturdy and understated while matching with the interior design.
• The master bathroom will have a stand-up shower with rainfall function and multi-showerhead setups as well as heated toilet and bidet. I will also have a clawfoot tub to relax in, if I see fit.
• Utilities will all have backup systems, and I will pay to have fiber optic cable run directly to the house for internet connectivity, with a minimum speed of 2.5 Gbps.
• The kitchen will quality upper-range appliances, including a gas stove, double ovens, a side-by-side refrigerator, and a dedicated upright freezer for long-term food storage.
• There will be a dedicated library and a dedicated computer room featuring high end computers and a rack server.
• I will pay for a maid to clean twice a week (and more if needed).
• There will be a working garage consisting of a conjoined 30x40 and 40x60 steel building that will house my workshop. In there will be a full woodworking shop, machine shop, material storage, paint booth (capable of holding up to a full sized car), flex space, and similar things.

Lifestyle :

• As a proud Gen-Xer, my style has always been "T-shirt and jeans." I prefer sturdy and long lasting clothing over fancy labels.
• However, I will drop some serious dime to have a couple of bespoke suits made, with hand cobbled shoes to go with.
• I wouldn't upgrade all my tech to the latest and best, but I will upgrade it to the latest that is sufficiently stable. Latest tech and new tech has a tendency to be buggy. I prefer reliability over flash.
• I will establish ties with the local community via cookouts and fun at my lake, so if things go bad, we all have each other's backs.
• A portion of my land will be dedicated to a community food garden, set up so the community pitches in to tend the garden and everyone reaps the benefits.

Vehicles :

• Daily Driver: A mid-size SUV that is highly rated and built solidly. I drive one now, and I love it.
• Fun Car: A replica 1957 Chevy Bel-Air, built with all modern innovations and safety features, with a modern engine and powertrain, but still maintaining the classic aesthetic.
• Work Vehicle: A pickup truck similar to a Ford Ranger or smaller F-150. Simple, reliable, and it does what I need it to do. No bells and whistles, either, because I am sure it'll get beat to shit just from use.
• I will also have an ATV or two in case I need to go offroad on the property and the truck won't cut it.

Vacations / Trips :

• When we do travel, it will be first class the entire way.
• We will take a big vacation once a year, probably 2-4 weeks worth, which will ostensibly consist of multiple destinations, but not be bound by any itinerary.
• Living on a lake, surrounded by forest is a good permanent vacation.

Health/Wellness:

• A therapist to deal with the stress of new wealth.
• Medical care to handle and correct current issues.
• Relax and make judgements on what else I need at a later date.

Personal Philanthropy :

• Close family members (those who I trust and respect, which are few) get a "Fresh Start" which includes all debts paid off, a one-time cash infusion of $1,000,000, and in some cases, a new, modest home. All of it will be done anonymously, of course, and this will be done to myself as well to throw off suspicion. After that, they are on their own to make something of the fresh start or just crawl back into a debt hole. No more handouts.
• My nieces will have a trust fund meant to pay for college in full, which includes all expenses except spending money, as well as emergencies. These trust funds will be set up so that they are capital gaining investments similar to my own and can ONLY use it for college/emergency purposes. The trust fund will be set up in their father's (my brother's) name. Any excess funds left over from college and emergencies will be paid out in total to my nieces when the youngest turns 30. Additionally, the trust funds will in no way, shape, or form be accessible by their mother, and the trustee will have strict requirements about how disbursements are made (basically, directly to the party accepting the payment, not to anyone else), and any requests for emergency withdrawal must be evaluated for genuineness.

Foundational Philanthropy :

• Every year, the Foundation will select, at random, a school district somewhere in the country to have all the school meal debts paid off, with a bias towards less wealthy schools. No child should go hungry because a school district is too greedy, too underfunded, or has misplaced priorities.
• Every year, the Foundation will award a full ride scholarship (tuition, room, board, fees, books) for people wanting to go into STEM, which will pay all the way through a Master's Degree.
• The Foundation will invest in the well being of the community by operating free clinics and providing meals and shelter for those that need it, as well as finding truly needy people and doing something nice for them. For instance, if a storm comes through and the end result is someone's roof getting torn off, the Foundation will foot the bill for that.
• Upon our deaths, our remaining wealth will being absorbed by the Foundation as a charitable donation.