I do it as early as I can and it makes me feel like a responsible adult, especially because I'm using one of the swaggier filing solutions instead of turbotax or whatever so it's nice and free
This time around it's a little more annoying because I have to deal with self-employment stuff from my gig economy job last year. But I actually might get a slight refund which I wasn't expecting so
Real tax heads do it using the IRS worksheets, no software allowed
I did it one year just to see if I could, it was hell, took two full days