In my opinion "catch-up" comes too frequently in this game and ruins the experience for the "average" player. The "main" purpose of obtaining higher stat gear is to take on more difficult challenges. However by time the "average" player is sufficiently geared and ready for the more difficult challenges, it is actually the lesser challenges that provide the bigger rewards. The system is fundamentally broken for the average player. Rather than "only" complain - I will eventually get to a solution proposal. Please read on.
When Heavensward came out the average player worked to complete the story, did the law tomestone / hunt grind, maybe began to dabble with Alexander normal / extreme primals and "possibly" even set their sights towards Alexander Savage. But before they could complete these tasks, 3.1 released. Roughly equivalent gear to Alexander Savage could be earned from Diadem, Void Ark, tomestones, etc. Just when the average player had the ability to challenge extreme primals, Alexander normal / savage, etc. - various "easier" options to earn "top-tier" gear opened up. Now lets say that player starts grinding void ark, diadem, tomestones, etc. and is finally geared and ready to take on Alexander Savage. Bam - 3.2 hits and mere tomestone gear now provides "better" gear than the raids the player just geared up for.
The average player thinks to themselves, why even bother? Why spend the countless hours gearing up to get to the party if the party is over by time you get there?
Prior to a new expansion release, there should not exist more "difficult" content that provides lesser rewards than "easier" content. I believe everyone should be able to experience the story which is why it is a good thing to have "normal" versions of "all" content. The game has normal / heroic versions of primal battles and raids. All it is missing are heroic versions of dungeons and then there's a perfectly viable solution to this problem. Imagine the below:
Patch 3.0: Normal difficulty dungeons / primals / raids let you earn up to item level 200 gear whereas heroic versions of each let you earn up to 210. Patch 3.2 - normal versions can get you to item level 205 whereas heroic versions can get you to 215. Patch 3.4, normal versions can get you to 210 where as heroic versions can get to 220. Patch 4.0 - expansion: everyone is caught up.
Is the system not broken when the content to earn item level 130 gear is "easier" than the raid content to receive item level 90 gear? Let's create incentive to actually play the challenges and then a year and half or two years later when an expansion is released - everyone is put back on equal ground.