To a new group GM or player, looking at 10 seasons of content is overwhelming. Where does a new group start? I was introduced to society as a player with #5-08 but I am confused how the starting adventure was fifth season, 8th installment. Is there a system or is it all completely random? Either way, what path should a new group take to catch up to main plot points and such? What can be or should be skipped? Is there any content that is required?
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Hello
the season only really matters for when it was released. You can still play them regardless of season. (the season does matter for a few things but not running them)
To a new DM with a new group I like running
First steps part 1: you are interns running around absolom
Wounded whisp: you are agents running around absolom
The confirmation: FIELD TRIP! you're real agents now, on your first field assignment.
To a new player you're kinda stuck with whatever comes up.
campaign arcs have been put together by fans to make longer stories.
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A "season" consists of all the adventures that were released in a given year of real time (from GenCon to GenCon, I believe?). Scenarios within a season are numbered sequentially in the order they were released, but are not intended to be played in that order--and in fact, they can't be. Paizo provides a mix of all tiers across a season, as well as within whatever handful of scenarios are the most current releases. That way, there is always new content available for every level of play.
After the first few seasons, there was a growing demand for starter adventures designed to introduce new players to the Society, Pathfinder, and/or RPGs. That's where First Steps, The Confirmation, The Wounded Wisp, etc., come in. From Season 5 onward, there's been at least one low-level evergreen released each year, to give more variety in starting missions (and to keep the veteran GMs from getting bored silly running the older ones over and over).
Each season has a theme that ties together several (but far from all) of the adventures in that season--for example, preparations for the Ruby Phoenix Tournament, or collecting the pieces of the lost Sky Key, or seeking allies among the elemental planes. Within a season, there are usually a few multi-part series to showcase that theme (or some other important plotline), as well as a number of sequels to popular scenarios from previous seasons. But with only a few exceptions, you don't have to follow any specific order as you play through the back catalog of adventures. (Although you may occasionally have to pretend to forget everything you know about what happens to a recurring NPC or location in later seasons.)
Threads like that campaign arcs one linked above can help you make sense of some of the connections between scenarios scattered across multiple seasons. Some players enjoy playing everything connected to a given plotline/faction/enemy/etc. with the same character, in order to have a stronger through-line for that PC, but it does require a certain amount of coordination with the other GMs and players in your community.