I'm definitely filling out a bracket this year. The only time I've ever won was when I played my dad's office pool in 6th grade. Only two people picked a Kansas - Syracuse final and I was the only one to pick Syracuse to win it all.
Ever since, I've at least picked Syracuse to go to the E8 and I've picked us to win it all 4 or 5 years. Needless to say, this does not end well for my brackets haha. This year, I might have a chance.
That said, I'd take losing my bracket every single year over missing the NCAAT, obviously.