It definitely needs to be evaluated on a case by case basis. I don't think there's really a one-size-fits-all solution. Or a single correct way to go about managing your funds.
For me, I started with an honest, sober look at myself and my nature. The Delphic maxim, Know Thyself, played a huge role. I'm impulsive, I have an addictive personality, and I'm good at talking myself into things to satisfy my need for instant gratification. If didn't do something to protect my funds from my own irrational and ill-advised impulses, I would have blown through it and been left with regret.
That's why it was so important to pursue the trust option in which I couldn't access the funds until a day much further in the future. And I'm glad I did. It has meant I've had to live within my means, and work for my living, but I know that money will be there for me when it's time to retire and enjoy life.