I was a youngin' when this happened, and I loved webcomics so I was paying attention to the scene. I hated CAD though.

Everything you said is right, and I want to add my own perspective.

The author took his uninspired joke strip where there was no plot, gave the main character (the self-insert) a girlfriend (and keep in mind, the self-insert was your typical no-personality nerd main character), and started to make a plot arch out of it. The girlfriend got pregnant, and this is drama. And instead of having any of the characters grow into people with personalities, he gave that girlfriend character a miscarriage. So he could get back to his no-plot video game joke strip.

It felt very much like those sit-com episodes where everything has to be wrapped up in a half hour, and nobody can learn anything because the show will go to syndicated reruns and be played out of order.

Miscarriages are stressful, emotional events, and he turned it into a disposable plot point. The girlfriend character had no real character development. She was a cardboard cutout introduced to be a girlfriend, and her suffering was used to neatly wrap this plot up for the strip.

It was loathsome. Just awful, unfunny obtuse nonsense written by a man with no ability to self reflect, and no intellectual curiosity about how other people think and feel.

I had always wondered how Loss became such a meme. The comic itself was rather uninspired and lame, and it was odd to me when the internet made it take off...although the memes about it tend to be mildly entertaining. Knowing the context behind it helps a lot.

Loss is from 2008, Rick Rolling started the year before. They're about the same age.