This will sound pathetic, and it's partially because I don't have much of a life, and spend way too much time with electronics, but one of my biggest regrets is---
Upgrading.
I've always fell for the increased security, and blah, blah, blah, but in the end I have a device, I once used, become slow, programs become useless, or my plethora of USB devises don't have the right updated firmware.
I have a Mac, and a MacBook Pro I'm thinking about wiping clean, and installing the original operating systems. It's just a pain, and yes--I know security is important.
I did finally learn on the IPad, but I'm still not completely sure I'm doing the right thing. I must have hit "tomorrow for 9.3.5---three hundred times. I just don't want to make this devise slower. I paid way too much years ago, and I hate putting things in my electronic graveyard--my closet.