$1 million each for my divorced parents. $2 million each for my two brothers. Good sized trusts for some friends who have problems with money and can’t manage it properly. A million or two each for some good friends who can manage their money perfectly well.
A slightly larger house (see below) in a quieter location - I love my current house, but temperature control is atrocious )freezing in winter and boiling in summer, and yes I have added insulation and it’s a brand new furnace and air conditioner) and it’s in a very noisy neighborhood. I like silence unless I’m the one creating the noise.
The larger house because I’d want completely separate quarters for my live-in personal assistant, whom I would never see except when I needed him/her - I’m flexible, so generally speaking a responsible, hard-working college student would do perfectly well. Day labor for house cleaning/laundry house maintenance, cooking/shopping, and yard work (including snow shoveling/blowing). (These would also be instructed to avoid me as far as possible.) Real estate is cheap here in Trenton, so a larger house in a quiet neighborhood could be acquired easily for under $300K or even $200K. A bathroom on each floor would be a requirement, as would a garage. Possibly a neighboring house for my Mom if she wanted it, and similar services for her.
Unlimited purchases from Amazon books and DVDs, PLUS unlimited Pay Per View and the Pay channels on cable. I hear about these amazing shows on HBO and Showtime, but I never see any of them.
If I were as I was a year ago, I’d also get a Mini S (I have a Scion xB), but I have apparently acquired chronic intermittent dizziness, so I drive so little these days that it wouldn’t be worth it. On the same note, travel is now not in the cards short of a drop dead emergency, and learning to ballroom dance is out of the question.
Extensive donations to charities and political movements.
Obviously, pay off any and all debts, including my mortgage. Pay my accountant to handle my investments entirely.
Possibly one of those huge flat-screen TVs, and upgrade to top-notch home theater equipment.
Otherwise, I’d live exactly as I’m living now. Possibly, if one of my dogs died, I might get a Mastiff or a Clumber Spaniel from a top notch breeder, and have a trainer in to train him/her in basic stuff.
This is one of my favorite private games - I win $20 million or better net in the lottery: what do I do with it? I figure I’d end up with $2-3 million net to live on after disbursements, and that would be more than ample for my simple lifestyle. I really don’t want to DO anything different from what I’m doing now - it’s just that I’d like to have the stuff I don’t do get done. And believe me, I do virtually nothing by most people’s standards, and would certainly want to keep it that way.