I always advocate for starting from season 1. Its a great cultural time capsule in a lot of ways and has a unique docmentary style to it that becomes less of a thing later on. More character focus, and "the game" hasnt developed yet which makes it different from anything else because "the game" was accepted as part of the experience immediately upon the very next season. And the ways the show evolves is part of the experience. Theres some stuff thats considered not so great television early on (late season 2, most of season 5 with some gems mixed in) but its all basically worth it for the overall experience. Like if I was trying to get someone into the show who was hesitant about it I might have them start with season 7 Pearl Islands (easily the best old school season and imho still the best one overall), season 15 China, or maybe Season 28 Cagayan if I think they'd be interested more in a more modern experience. There's also season 16 Micronesia and season 20 Heroes vs Villians, but those involve returning players so I feel they cant be properly experianced without seeing their previous showings. But those are both also top tier seasons. But if you actually find the basic concept interesting, go ahead and start from the beginning.

(Also hey if you do end up doing this, try to remember to DM me your thoughts. Or even add me on discord if you have one. I'd love to talk about it. )