Hindsight is 20/20, but I've always thought that were I to come upon a windfall of some large(ish) caliber, I'd likely not tell a soul, and not change my lifestyle significantly and suddenly. Sure it's tempting to run out and buy a Ferrari, but if one thinks about it, those are childish wishes and whims - a lack of self-control, if you will. The first things I'd do is settle all my debts (house, car, etc.), which aren't as visible to others. I'd also start winding down my employment (i.e. 1-month or even 2-month notice).
By simply slowing the transition down significantly, perhaps even "embellishing" the nature of the windfall (i.e. "I just closed a deal that's going to do very well for me over the next 2 years") such that the changes are logical and incremental vs. sudden and drastic, one can avoid such "acclimation pains" in one's social circle.
In the end, if you change your life drastically there's a very good chance you'll run into the same isolation issues - windfall or no. So it's about the (perceived) speed of the climb, not the steepness.
Besides, if you make the change slow it's easier for people to see that you're not changing - just your lifestyle and economic conditions. Less scary that way I think.
PS/ what's he bitching and whining about women for? he can afford any (set of) pornstar(s) he wants now!!