You can run any dungeon in explorable mode with rare quality gear without having any issues whatsoever. But if its really a bother Exotics can be acquired in a day or two.
In sPvP gear doesn't matter. In WvWvW it rarely matters as most of the time you fight in huge numbers but still, getting the need "max" gear ain't hard.
General pve and dynamic events require gear even less as you can run fully equipped in Masterwork items and still perform wonderfully.
Only place gear comes to matter is Fractals dungeon, but that's only on 10++ for exotics and 20++ for ascended. But to be fair, if you don't find it fun to play the dungeon then there is no need to actually do it No point in reaching better dungeon lvl if its not fun for you.
And there we go. If things as prestige and legendaries are on your list then its a terrible reason and all that is your own choice and no one is making you grind for better looking pants.
Or am I missing something? I'm slowly going for my legendary but I haven't seen a single thing I would be required to grind for if I didn't want to myself.