Even without any help or the new easy gear, you would never have been too low on ilvl if you just got the gear you were supposed to. You get enough tomestones from each set of content to reach the next ilvl requirement, every time.

And again your mistake was to think that you should be rushing through the story to "play with friends at level 50". There is no difference whether you're level 1 or 50 in terms of playing with friends, since the level syncs to the content anyway. What your friends are doing in the expansion content is exactly the same as you're doing - the story, with occasional multiplayer dungeons and bosses. And the story IS good, not that you would know if you skipped most of it.

In short, your bad experiences are 100% self-inflicted.