Sounds like a risky route. If you approach random women, you can't immediately ask for sex. You have to entertain them to outings, vacations, etc like you said. By that time, they'd already know you're loaded and if they're the gold digger type (exactly the type you're looking for), then the first thing they'd do is sue you for all the things they can, and try to take your money. Also, it's pretty creepy to approach strangers, most will tell you to F off, so you won't even make it that far. I used to approach random women for regular dating in my 20s (1000+) and this method of building a connection with a random stranger didn't work. Most say, they gotta go somewhere, bye. I say the same thing when strangers approach me for whatever reason in public. Bye, gotta go!
SPs and Sugar Babies are the only routes I know of, and for Toronto, it's useless b/c both these routes have low quality women. Very different than 5-10 years ago when so many girls in their 20s were into this.
Therefore, for hook up purposes, winning a lotto max is worthless. You;d have to travel to other places where you can find SPs in their 20s.