Flair can't do agent work, he never could piece together a match. He just went out to the ring and called it out there. Most of the all time greats in anything can't teach people what just came natural to them. As for ambassador work? Nah, Hogan is far more trustworthy in that role.
As for Flair not saving his money? Yeah.....That's what made him Slick Rick, he wasn't playing a character, he was/is that guy. The maturity level of pro-wrestlers depends on the age they start on the road. You start out young, and that's all you know....you are going to act that way the rest of your life. Especially if you don't have an other outlet or life outside of it. Flair never left pro-wrestling ever....This is what he has done since he was 18.
The one thing that bothers me about people who use the term "legacy" and I am not directing this at anybody, just see a pattern amongst the IWC is that they are the same people who eagerly shun them and cry about young guys not getting their due, and how they deserve this and that....Like the guys who paved that road they are riding don't deserve anything too. And callously just act like them not doing well financially is all their fault....Like they don't even factor in things like they have to pay for everything...Hotels, rental cars, food, gyms and then have taxes and licences to pay in every state they go, and stuff they have to pay for when they leave the country.
Think the guys in the territory days, or 80s and 90s had financial planners? They didn't even have agents or lawyers to advise them on what how they could plan for the future.