First time I played WoW I liked that you were given a guided tour of your races homeland as it explained the world. The last time I played WoW I had to to a tutorial island that explained nothing about the world and then dumped me in an expansion with characters I had no fucking idea who they were and why I should care about them. Even ESO doesn’t prevent new players from playing the base storyline and FFXIV still requires you to complete ARR before moving to the first expansion. I dropped WoW pretty quickly again because I felt too lost.

You seem to be knowledgeable about FF so I ask, is it a good time to start playing? I feel like there’s a lot to get through before I can get current in time for the new expansion. Is there something I can boost like in wow to get current. Without that then while I can afford it, it still feels bad to pay a sub for old content ya know.

No. No way to skip the story as far as I’m aware and it’d be a bad idea honestly as the story continues right from ARR to all the expansions, endwalker has a lot of callbacks to everything before it as it’s a swansong of something like 8 years. Dawntrail is the first new major story arc since FFXIV’s release. Leveling isn’t so bad currently because it’s boosted to get as many people to 90 as much as possible but there’s no max level item either as far as I’m aware as you pick a class then that class becomes a specialisation so you’re constantly getting new abilities to learn for your rotation. It would defeat the point of learning your specialisation if you skipped the leveling and quests of it to max level and had everything unlocked.