If the win was a huge jackpot one I'd buy the dream small-holding with a fair bit of land attached. It would have to have a main building like a decent size farmhouse or barn conversion + at least 2 other buildings suitable for residential use. My better half would like all sorts of animals, but if dreams could come true he'd have a few alpacas and llamas so that they could 'hum' to him every morning. There would be plenty of garage space, barns, sheds, workshops, a forge, a mill and scope to build anything else the pair of them decided they'd need to make things, do the restoration projects they've been thinking about. There would be some woodland areas, maybe a small river/stream, where we could set up a woodland guardians group to teach skills and provide a safe environment for groups of people that would benefit from time with nature, with animals (e.g. kids that have been abused, people with mental health problems, people with disabilities, homeless, recovering addicts, rehab after serous injury or PTSD). I would also love to have the funds so that my better half and his business partner could head of to Alaska or the Klondike and spend 6-months- a year gold mining, diving and/or dredging for gold. I'd miss them terribly but if I was ever in a position to help them live their dreams I'd be happy to give them everything they needed to have a great experience - I'd even throw in a motorhome so they could travel in comfort or be OK 'on site'. They'd also get driving experiences, flying lessons and things like trips in Spitfires, going to space for zero-gravity etc - with a big enough win they could buy the car/plane/helicopter once qualified. They'd want other toys like drones, ride-on lawnmowers (for the bits not naturally 'cut' by the horses and other grazing animals.
One residential unit would be for my better half's business partner /friend - at present he'd be happy with a log cabin/small 1-bed place, but I'd like to future-proof for him just in case he ever gets a partner or decides to marry or ends up with a child or several children. A stable block would be a high priority for him and the rest of us would quite like that too, complete with stalls, tack room, shower room, boot room + a paddock, grazing fields and all the equipment needed to care for the horses and ride them safely
The other building would be so that our current neighbour could become our new neighbour - she has always dreamed of living on a small holding, having horses and the space, time and money to be able to rescue animals and provide suitable forever homes for them. Sure she'd be welcome to share the stable facilities and to have at least one horse of her own. Her place would need to be minimum 2-bed, preferably 3 so her grandson and his family could come to stay with her. If there was scope to have a few buildings as 'holiday lets' or as part of a business her grandson could stay there if she had a smaller home.
I don't need that much for myself - room in the house to have a library (built by a master carpenter - the men could help) with parquet flooring, hard-wood floor-to-ceiling bookcases, wood-panelled walls, lovely big desk, choice of comfy chairs. lamps, rugs, tapestries, office space well stocked with good quality stationery and I'd spend a lot of my time in there while they built things, made things, spent time on their various hobbies.
All 3 of the aforementioned people + a few family members & friends would be treated too. It may sound like a large chunk of 'my' winnings would be spent on others but it's not really all for them, I already require a fair bit of care and this will increase as time goes on. It would benefit me greatly having them all there, give me all the personal care and general help I need + the money would enable me to buy in help when I needed it or they were away for a bit. Buying them all a new car would mean reliable transport and the likelihood of at least one of them being around to give me a lift if I ever have to go anywhere or need to be taken in to hospital
The cats would be spoiled rotten, with beds, scratch posts, secret catflaps to get around the house. I'd pay the guys to custom-make homes, fencing, etc for all the animals we'd get - bespoke bird boxes, bird baths, bat boxes, hedgehog houses, bee hotels, insect hotels. Making a lot of the furniture for the new homes would keep them busy and use all their new buildings and equipment. I'd end up with a house built from love by the people closest to me and also have them as my closest neighbours. I'd be happy and think we could all live there happily together.
Please excuse any rambling and/or typos - had a rough night and not slept yet! Interesting idea for a thread