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 
Oh I guess I've never run into that since I've always been in the same software
Smarter than me, but it's okay, only one or two days of stress. Worth it to spite the tax prep industry.