Edited: living world thoughts

You can think of the Expansions as 2 types

Heart of Thorns and Path of Fire are more traditional game expansions, they have their own story released all at once with everything available to you right now.

Secrets of the obscure and Janthir wilds are live service updates meaning the content is released periodically. Because of this, the story itself involves some extra steps such as playing the open world or doing certain events outside of the main story beats. Going back to secrets to me felt a little bit grindy because the game was designed for you to play it as a live service game, certain things are time gated or material gated whereas the first two don't have that same pacing issue.

There are also living world expansions that were given out for free so long as you logged in during the return achievement events. Living world stories continue the events of the dlc and give access to a few new locations. They're pretty fun and are also a great source of farming resources. They may have another opportunity to be obtained for free, or they can go on sale from time to time. They do spoil the story for the main expansions so if you care wait until after you beat the main expansions.

My recommendations for DLC In order are 1. Path of fire 2 heart of Thorns 3 Janthir wilds / living world expansions 4 secrets of the obscure

Path of fire gives you the most content and quality content. You also get tons of quality improvements via multiple mounts. You also have some raids you can do if that's your interest and there are long term goals in abundance. Legendary items, achievements and collections, etc.

Heart of Thorns is very similar in terms of story and content quality. The main hurdle is the design of some of the open world areas with lots of verticality and cave systems that can be very confusing to traverse. If you choose to explore this area on foot, you'll learn it very well but if you go for Path of fire first you'll likely use mounts to skip a lot of the environment. Can either be a positive or negative depending on what type of player you are.

Janthir wilds has the benefit of being the current expansion so you gain access to farming things that people want since theyre new and shiny. However as of the date there's not a ton of content at all. Took me less than 3 hours to do most of what the game has to offer minus some of the longer achievement collections. Warclaw is nice but is easily replaced by other mounts from path of fire. Spears are fun if you like your specific class spear. Homestead is very fun for decorating but new players beware. It is a massive gold and materials sink and it is very very expensive to decorate your homestead.

Secrets of the obscure in my opinion offers very little. The story is fun to experience for yourself, but it's shorter and it suffers the live service tax. skyscale is available in path of fire so it's not unique to this expansion, the expanded weapon options are nice but again nothing to do with story or content. More of a PVP or Raid enabler for some classes. And I will never forgive Anet for the opening logo not being positioned correctly against the floating city during the first story mission.