I've only just realised you were referring to hbomberguy here. I thought you were referring to Matt Myers. hbomberguy's been brought up a few times in the
Let's Players originating from Something Awful thread. I myself wrote a bit of a
polemic on him there. I don't think he's done enough yet to classify as a lolcow, but give him some time and that could well be the case.
You mention the guy's sense of humor basically being LOLSORANDOM and I'm glad other people see it. He seems like TGWTG knock off and I see him pal around with that lot on twitter so it doesn't surprise me one bit.
Also:
One of the core criticisms of Channel Awesome has always been that it was a circle jerk and that's still true. If you're not part of the club or don't actively try to kiss their asses in awe of their glory nothing you do is worthwhile to these people. It's such an incestuous little shit hole. They basically squandered their peak relevancy (2010-2011) making videos that were entirely indistinguishable from the next. Hell the only difference between a Linkara video from 2010 and 2017 is the couch and whats behind it. When they should have been focusing on improving the quality of their videos, honing their craft when it comes to writing, comedic timing, and general technical videography stuff they were instead doubling down on running jokes that became increasingly alienating to new viewers with each successive call back, turning silly skits designed to illustrate a point into embarrassing story lines that strained your ability to take their criticism media seriously, and wasting weeks of their producers time making shitty anniversary specials and grainy looking crossovers filmed in dimly lit hotel rooms. The site had an almost bizarro-natural selection where bad ideas propagate and thrive in the group while good ideas die out.
During their peak relevancy they bloated the site roster with any dead weight they could get their hands on, diluting what it meant to be a Channel Awesome Producer to the point where it basically became brand homeopathy. Once upon a time the site was pillared around a few big name producers who got to be their "film guy", "comics guy", "retro games guy", "modern games guy", "the girl", etc with some smaller producers filling out more niche roles. The more producers the site added the less distinguishable their big names became against a cacophony of 1,000 Diamanda Hagans and Blockbuster Busters. As time has marched forward people like Spoony and Lindsay have parted ways with the site but they're still stuck with a lot of that weight.
By 2012 it was all so worn to death and combined with the fact that they were always so smug and unpleasant towards their fans it's easy to see why so few people who are fans of them today have been fans from the start. When the content is that fucking stale and the people making it treat you like shit on twitter for even mild disagreements about fucking video games (here's looking at you, Spoony) there's little incentive to stick around.
Jon and the creators that he networked with and is adjacent (namely Normal Boots, Hidden Block, and Game Grumps) outclassed them in every imaginable respect. People like them and Red Letter Media sent Channel Awesome into the slow motion death spiral that continues to this day.
So yeah, I'm guessing they're double salty over the fact that one of the guys who basically killed their monopoly on this style of video isn't interested in toeing the political lines they're embraced in the last few years and instead seems almost interested in actively transgressing it. Even more so that it doesn't seem to be hurting him like the Spoony rape joke debacle hurt their own site.
Also, fun fact, Diamanda Hagan, whose content is so bad I can't make it through an entire video, used to be a contributor at the now defunct Channel Awesome clone "Reviewtopia" (later RVT) which Short Fat Otaku (the guy behind those Gamergate "Indie-Fensible!" videos) was also a part of. That site had a world class Nuclear meltdown a few years after it's founding but years later Short Fat Otaku claimed that, when the site launched, one of the contributors they rejected was JonTron, and the timeline of when that would have happened actually makes me believe that's why he founded Normal Boots.