The reason Lowtax had internet fame/wealth is AUTHENTICITY.
I think I get where you're coming from, but I think your analysis is headed in the wrong direction regarding Lowtax's noted obsession with "authenticity".
Lowtax had fame and fortune because he came along at a time when there were very few comedy sites online, let alone ones that operated as "professionally" -- paid writers, recurring features, a format that didn't look like a Geocities page, etc. -- as SA did. They were a big fish in a small pond. It had little to do with authenticity -- and indeed, wanting to remain "authentic" eventually became Lowtax's buzzword he'd trot out to justify NOT changing with the times and keeping SA relevant which, in turn, sank his fame and wealth. Monetize Let's Play culture? Nah, dude, gotta remain authentic. Transition to videos instead of long-form text articles spanning multiple pages? No. Muh authenticity. Branch out by hiring some content producers outside of SA's usual WACKY ZANY wheelhouse to broaden the appeal? AUTHENTICITY NOW AUTHENTICITY FOREVER.
He simply never moved on and just thought that if he just did what worked initially hard enough, it'd always work by sheer force of will; he was also too lazy, drunk and/or pilled up to spearhead any sort of rebranding or retooling even if he'd wanted to. But the internet did move on, and eventually the novelty of funny photoshops and OMG PURPLE MONKEY CHEESE XD text essays became commonplace. Then it became old. Other contemporary sites like The Onion and Cracked did their best to catch the next internet comedy zeitgeist -- video, as spurred by Youtube -- but they largely failed
because Youtube came along and cut out the middleman; content creators could create whatever they wanted (not constrained by SA's shitty management and low pay, or Cracked's listicle format they came to use as a crutch, or The Onions "it's a newspaper, but wacky" gimmick) and monetize it, in far more digestible video form. Throw in Facebook and Twitter and Vine/Tiktok and Instagram for additional content platforms, along with Patreon, GFM, PayPal, etc. as ways of monetizing literally anything, and the era of the Big Monolithic Internet Humor Site came to a close; just as malls replaced department stores and online shopping replaced malls, SA was replaced by platforms that did what SA did, but better, sleeker and with more potential payment for creators, and those platforms were themselves replaced. By as early as 2009 or 10, there were tons of platforms that did everything SA did, but better, sleeker and more modern, and without the dysfunctional management culture; as a result, SA began to experience a long, slow heat death over the next decade and is now effectively dead, the (there's a) front page(?) now an internet ghost town. The Onion has limped on, and a few very mixed media niche sites still remain (The Hardtimes for music, Reductress for feminism, etc.) but who gives a shit about Cracked or Seanbaby or Old Man Murray or SA's other contemporaries these days? Could SA have limped on if it'd had better management and a less batshit customer base? Probably. But yet again, rather than make tough changes and hard decisions, Lowtax preferred "authenticity" which at this point was just stubborn, self-destructive complacency. In a way, that's what "authenticity" always was.
Even during its heyday, SA was on borrowed time because of the nature of humor and the internet. It had to adapt or die, because trends don't last forever, especially online. From MDE to Twitch, this thread is full of examples of ways Lowtax could've branched SA out from photoshops and walls of (ostensibly) funny text. He refused to adapt *because* of his desire to be authentic, so he died; metaphorically first, and now literally. No one outside of himself cared about SA being authentic and it certainly wasn't why he got rich/famous. People didn't come to SA because it was "authentic"; they came because they wanted to consume funny
memes image macros and 5 GOLDEN MANBABIES threads and funny photoshops, and some talented folks who happened by ended up staying and creating more; then, eventually, they wanted other things that SA couldn't or simply refused to provide and so they moved on. The last vestiges of Something Awful are now consigned to a few Youtube creators and a bunch of Weird Twitter posters. Ironically, despite their much smaller status, they're probably all being compensated better these days, because paying creators 40 bucks/article (when and if he remembered to pay to begin with) was another way Lowtax stubbornly remained "authentic" (as an aside: consider how the lame ass furry apology article netted its troon creator the same payout that a legitimately viral thing like Smashmouth Eat The Eggs did its creator; is it any wonder why Lowtax couldn't keep talented people around?).
Lowtax's wealth was due to the longevity of SA, keeping costs low by severely underpaying his staff and several years of pity/nostalgia-fueled Patreon income. If anything, it (and eventually his life) were cut short by his obsession with being authentic.