Russo’s WWF departure in 1999

Im hindsight, one of the worst professional decisions ever made? Dude is literally doing a 24/7 podcast now to pay his bills for a few old AE die-hards

I don't think so.  He was burning out in mid-99 and was likely nearing the end of his usefulness to Vince anyway.  At least the WCW deal gave him a financial cushion that he wouldn't have had when he was inevitably tossed aside like garbage by WWE.  Also, going to WCW allowed people to actually know who he was, for better or worse.  If he was just some anonymous writer in the WWF who got fired or quit or whatever, he'd be a trivia note years later where people would be like "Did you know former WWF magazine editor Vic Venom was actually a writer for the WWF for a few years under his real name of Vince Russo?"  and that would be it.