So, pretty dead lately....

[Glasya]

The only problem is that something like that would rapidly turn from "something to work toward in your spare time" to "something that has to be ground out so you don't get kicked from parties for not having it".

Well you dial it in. Maybe remove the secondary stats or something.
Again, these are just ideas. But I'd argue that gear shouldn't just be thrown out once its iLv becomes outdated. There could and maybe should be gear yet released in Heavensward that, but virtue of its auxiliary effects or procs alone, renders it superior to the (solely) numerical bonuses of much higher ilv leveling gear in the next expansion.
And is there anything wrong with having certain pieces of gear be mandatory? In this context it's not like there are players without access to the Gold Saucer. If you aren't at a point to be working on content like that then you aren't at a point for it to be considered disadvantageous.