He's a big fan of Owen Benjamin and that is one of Owen's tactics for generating a community feel, as you say. It's understandable but not very entertaining. I think Owen interjects jokes earlier to keep the entertainment levels up.It's a strategy to acknowledge those who pay him money and create a community of sorts. Not sure why he does it. No other YouTuber feels the need to do that.
As much as I like Rowan, it smacks of desperation
I contribute monthly to Rowan (just the basic 5 euro) and think he's a great guy just think shorter videos might be better. You need to be really clever (Vox Day, GFP) or really funny (Owen Benjamin) for me to watch 1 hour streams regularly.
Rowan is a big fan of Vox Day as well, he's posted a few superchats to him recently on his live stream.