I don't think it's all that abstract. Lowtax is just fell into a good thing and then never did anything with it.
When the internet just started to take off (late 90s, around the time of Lowtax's first "webmaster job") there was a lot of confusion around how businesses would exist on the internet - there wasn't a lot of money there initially and no one really knew what to do. Ads were the only source of revenue but it was in no way the same as it is today; for a number of reasons (poor tracking, poor ad loads, no where to drive traffic to, etc).
Something Awful thrived in this envrionment - when having an active message board was a "big deal" as well as constant content generation that Lowtax stumbled into. It was such a "hot spot" Lowtax wound up being able to charge $10 for new users to sign up and participate in the forums. He was able to essentially segment out his users into subforums and inadvertantly created specific, targeted advertising groups. With his new found windfall, he hired an IT person (Radium) and was able to pay (not a whole lot) actual money for people generating content by paying the front page writers - he had essentially turned Something Awful into a business.
But then he just kind of stopped for reasons we'll never know and while he was one of the first to market, he gave up that lead and started his long slide into obscurity. His main issue is that he never kept pushing forward - he never grew the business while his competitors did. He watched as his content creators went over to other sites (youtube, reddit, twitter, facebook, etc) and were able to monetize much more effectively without him. Everyone seemed to like him, but the story was always "I wanted to work with him, but the money wasn't there" - even when the money was there; as SA was making gigantic stacks of cash for many years - Lowtax simply wouldn't part with it. He got used to the idea that everyone would do everything for free. He also did dumb shit like buy a big house, a fancy car, and got married without (allegedly) any kind of pre-nuptual agreement.
As the web continued to evolve, money became a larger part of it - if you're running a "serious business" you need to pay your people. Not just content creators, but also your moderators and merchandise people - which Lowtax was just unwilling to do. Merchandise became (and still is) a huge revenue stream for websites, but Lowtax half-assed it to a point where he lost tons of business and became regarded as a joke. 90% of this thread is pointing out what an absolute shit job that his unpaid staff (moderators, admins, and volunteer systems administrators) but it bears repeating - even kickstarter games have paid moderators for thier forums.
TL;DR = Lowtax always did the bare minimum and didn't even do a good job of that - where as all of his competition grew to be much more attractive to professionals, audiences, and creators. They all left him because he was stingy and lazy.