The problem with constant upgrades is that players joining late will always be behind, because they will have to catch up everything you already done.

That's not how MMOs are supposed to be if they want to remain appealing to new comers. Every now and then, itemization progression should be "soft reset", either by raising the level cap, either by releasing new tier of gear (and making the previous tier/or something equivalent to the previous tier easily obtainable.).

That way, someone starting will have a chance to catch up and won't be discouraged.

It still drives me crazy in XIV that all that time my and my ls spent last October was a 100% waste of time.
Getting gear in a MMO is a waste of time then.