That was partially my intent, so thank you! The whole thing was done in a few hours--almost exclusively research--so not saying this is a great project or anything but here are some ideas to skim.

The inspiration? A recent article questioned the accuracy of some the story (certainly parts are exaggerated). The article's author, a fan of HST, believed that many placenames had likely been changed. And from that, 'who knows what else'. When I found the address for the hotel mentioned, the story seemed more plausible (rightly or wrongly) and more tangible to the Derby of today. I felt these details were important context and that their inclusion could be, as you suggest, a significantly different experience. But, and I do hope this is the case, perhaps their presence could result in the reader/user being more likely to believe the author.

I decided sidebars, inline/side footnotes, endnotes (even in printed products) and tooltips are too distracting. The least distracting seemed to be hyperlinks in a somewhat subdued but still accessible style. (Having them hidden until interaction--like in the focus modes of some text-editors--was tempting but I wanted to avoid hover states.) Ideas from anyone on less intrusive ways of including asides are appreciated!

So I wanted to give context but, as TVTropes and Wikipedia demonstrate, links can lead a reader away from the primary text. Knowing this, I decided to go ahead and create a flawed experience and intentional demonstration...

This was the first article to be called 'Gonzo'. The word was coined after its publication and so it represents the beginning of a style, widely imitated, that HST would stick with for much of his career. If this is a foundational text for the genre, what characteristics make it 'gonzo'? I guess one of the main characteristics is that rather than give a detailed play-by-play of the horserace, HST instead gives details about the spectators and his own misadventures (resulting in a frank admission of unprofessionalism). These details are specific: rather than say he had a beer, its a Colt45 malt beer, just as a suspect might overcompensate with details in an interrogation with police. And he goes on to namecheck company after company (after Ian Fleming but before Tao Lin). I wondered: what would it look like if HST were drunk at the Kentucky Derby today? His namecheckings and frustrations might be expressed as at-replies on Twitter. This Gonzo post might be lost in the millions of blogs. This struck me as funny (tragic?). To allude to the odditiy of seeing a written work designed for another era and its mediums be tied and fragmented in hypertext, I linked 'Hertz' to @hertz (kinda absurd, but a fairly common practice) as well as a few others like that. It does seem harder to take the words seriously as a whole when there are basic (maybe ironic?) links.

So I had hoped to provide context and I still think much of it is useful, but based on design limitations surrendered to the idea that this was desecrating an experience many are used to. I ultimately found it incredibly amusing to picture HST crafting hyperlinks in some bloated Soviet CMS to link to a YouTube video of teenagers signing as perhaps the HST of today is currently doing.