Item level compression in Heavensward?

[Teslo]

This isn't needed until you like have 5-6 expansions.

It isn't needed at all if you plan ahead for it. Hopefully SE has a plan in mind to keep this from being required, like they just had to go through in WoW.

The problem with item compression is that, while it works the first time, eventually you'll need to do it again (Sooner and sooner, each time). After 2 or more, the low levels start bleeding together and it gets to the point where iL55 gear is 1 or 2 stat points less than iL90. Then the next time iL55 is 1 or 2 stat points less than iL120, etc... This isn't NECESSARILY a huge problem, since all that gear is essentially worthless at that point anyway, but from a logistics standpoint it seems awfully foolish to me. My 2gil.