The sad thing is, I've been reading this guy's blog for over 10 years and your summary there is about as vivid as I can recall him going on about his 'adventures.'
They're not stories or posts with lots of colour, details, emotion, feeling or anything of the sort. It's just a grey list of checkpoints as you laid them out.

The blog it a box of mechanical bits of information on what a guy did. There are too many posts for anyone (especially new readers) to go back and digest, and the way everything is written isn't interesting enough to bother, apart from a few "out of the box" articles here and there, like the one about buying the island, or what not.

The guy says he's a writer, as well.

Being a good writer doesn't mean doing lots of whacky things. Being a good writer is being able to connect with your readers and being able to make even the most mundane thing interesting to read.

Tynan has somehow achieved the opposite: he's been able to mostly create a blog about a VERY interesting guy with a VERY interesting life full of VERY interesting things kind of uninteresting. Not boring so much, but it's like a meal without any seasoning. It's like a piece of fried chicken on its own.

It's quick. You can make several of them at once. You can freeze them so there's a backlog. It's got SOME nutrition to it. But there's no colour, no fragrance, no real flavour... and it becomes a chore to chew it.

Again, I don't mean to sound entitled as he basically gets nothing from the blog; we're not paying him for his posts. Well, perhaps that's not strictly true since all his coaching and Super Human clients/customers come from the blog.

But I think Neil Strauss wrote in his book that Tynan was someone that got distracted by shiny things or toys, or something, moving from one to the next. I think it's the same thing with his blog: his obsession for optimizing stuff has its detriments: fawning over optimization experiments to the point he would just pump out blog posts in bulk REALLY hurt his writing ability, I believe, and turned his blog into something akin to a "self-development, life hacker McDonalds" type fare.

I think he's quite sure though that the blog is his playground, not somewhere to write well or be read well, though?

The sad thing is, I think Neil Strauss wrote about Tynan's life (if only a period) better than Tynan has about many of his pursuits. And that was such a long time ago, and arguably what put Tynan in the public eye and was a precursor to this blog and many pursuits.

I would think that getting out of that shadow would be a worthwhile endeavour. Nobody knows Tynan like Tynan and his life has been SO much more interesting than the Project Hollywood days.

But for someone that's so passionate about his life and loves it, none of that passion, energy or life comes across in his writing.

It's just an exercise of posting for the sake of it.