The faux-chronological order totally mimics the lifespan of something like the NES: The earliest games are really experimental and lacking in design or aesthetic depth. (In the top row, Mortol inspired a sequel, which tracks as I'd say it's more polished than the others.) The final row, by contrast, has attempts at idle game elements, voice samples, and however you'd describe Mini & Max's world.
There isn't a "right" way to try out the games - I think chronological is great in the spirit of experiencing the LX as a fictional gaming machine, but like MCBanjoMike said, the first row games are quite a bit rougher than the others. If the experience is available to you, imagine you're a kid at the video store again. You don't know anything about these games except the cover and the back of the box info (conveyed here by hitting the B button) - which one looks appealing to you? Luckily, there are no wrong answers - you already own all 50 games so you can go pick something else out.
One other thing I've noticed in the way people (myself included) rave about this game is that it's a love letter to lots of things - the NES, Newgrounds Flash games, single-developer indies - but it's also a love letter to jank in game design, in all its forms. Throughout the collection, quality-of-life is more reflective of a game released in 2024 than the decidedly 80s timeframe of these games, but the intentionally strange design choices abound. The silent hostility of Barbuta is an obvious case of this, and Combatants' brokenness a slightly less obvious case, but it's everywhere: Bug Hunter feels like a converted board game, Planet Zoldath seems like a cult DOS game for reasons including irritating hit detection, Kick Club/Fist Hell/Rakshasa/Star Waspir are all representatives of "Nintendo-hard" games that resist easy playthroughs, and the physics in games like Onion Delivery and Camapanella 2 seem like catnip for high-performance gamer sickos. I absolutely love this collection, but I appreciate more of the individual games than I enjoy playing them. (This is in contrast to Retro Game Challenge which was all killer no filler by design.)
The last thing I want to gesture at is the metagame and secrets through the Terminal codes. I'm a sucker for lore generally, and it's great to have at least tried about 30 of these games before finding answers to questions like "What is UFO Soft?" or "What is UFO 50?". Don't rush into it or anything, but going through it has helped contextualize individual games as well as the general arc of the system.
Personal faves by row: Mortol, Avianos, Party House, Grimstone, Mini & Max