If I won the lottery, and money was no object, I'd continue my current plan, which is: SR20 -> SR22T and then MAYBE add on "-> Vision Jet" last, after many hours getting proficient in the SR22.
I got to see the inside of the SF50 recently, and of course it's a very cool plane. But I'm single with no kids, and don't do a lot of hauling people around, and I think it would be almost too much plane for me. Just too much wasted space and room I'd never use. If anything, I'd want it more for the increased capabilities, pressurization, etc, than for any increased people-hauling ability. Part of me also thinks I'd prefer to slow down a bit and enjoy the trip. I could easily see if I spent lottery money to get a new fully loaded SR22T, being perfectly happy in that (jeez, who wouldn't be???) with no desire to upgrade to the jet.
But I'll never win the lottery, so I don't have to burden myself with such decisions