I'd been getting by for a long while with 16 tracks on a Yamaha arranger keyboard and then recording the output of that plus live vocals directly onto a CD recorder, which could be frustrating to say the least, though at time( after many takes) I thought some turned out okay. Then I bought a pc with a junior version of Cubase, as I'd read/heard that this was the way to go. I could barely get a sound out of it and it seemed to crash a lot, probably because I was doing something wrong, but the customer support was appalling. The response to any question I asked was expressed in a way that I couldn't understand despite my having explained that I was a total noob and needed a press this, click that type of answer. Their final answer was that it was impossible to explain it any differently than they already had, so I soon gave up and went back to my tried and trusted method.
Eventually, probably sick to death of the same song over and over, Mrs Paulo booked me a day in "a recording studio" as a birthday present. It wasn't so much a recording studio as a guy with some gear in a shed, but he was running this thing called Sonar 2 and when the day was over I left thinking that I had to find a way to get me some of that..... so I did, and that was that.
Like many, I **** and moan about it from time to time, mostly when things get "improved" in a way that actually makes it worse, but in truth what I have now is beyond anything I could have imagined owning back in the day. I just wish I could have had it all back then and also had paid more attention to the guy who manned the mixing desk when we played, who at the time I thought just turned a few knobs a slid things up and down with no discernable effect just because he could. Maybe he did exactly that.....I was winging it most of the time, so who's to say that he wasn't ?