The pun is genuinely clever. "High score" as in the leaderboard and as in getting high to finish the score. It took me a couple of seconds to land and then I really appreciated it.
The title screen is well made, a PC monitor with the logo on the screen and a cigarette crossing the I in HI, with post-its stuck around the frame. Proper scene building. The menu having Start, Credits and three separate volume sliders for Music, Voice and SFX is more than most jam entries manage, and having a Voice slider at all signals there's actual voice acting in here, which is rare. The two pixel art anthropomorphic characters in gaming chairs with the keyboard and mic on the desk are funny and well drawn. And the opening dialogue is exactly the tone the page promises.
Also, your end of life plan is one of the most thorough I've read in this jam. Browser build plus a Windows download plus source on GitHub so anyone can update it if it stops working on modern systems. That's the actual answer to the question.
Three notes. The "Start the Game" button didn't respond to my first clicks, it only worked after insisting, which is a pattern I've hit across a lot of entries here. The dialogue advances one bubble per click with no "click to continue" indicator, so you're never sure whether it's frozen or waiting. And I didn't reach the actual playable part in the time I gave it, the intro runs long, so a skip intro option would help people who are voting through a lot of entries.