@JacksonMo, I get where you're coming from on this.
I don't know if I'm unusual, but I actually enjoyed the gear progression. When I only had a couple pieces of Columi, SM EV was hard for me. I had to get better at my class and learn how to coordinate with others in the group.
The same thing happened when I first started SM EC. I was Rakata/Columi and it was a significant step up in difficulty. I really had to pay attention to what was going on, move when I should, stay when I shouldn't, switch when I needed to, etc. etc.
So effectively, as I became a better player, it "unlocked" the higher levels of content I could complete, which allowed me to get better gear. I suppose this sort of experience isn't for everyone, but I really enjoyed it.
On the flipside, imagine running SM EV for the first time in Dread Guard? Any halfway decent player would find no challenge while vastly overgearing it. Anyone finding it difficult in that gear would likely be so clueless at their class it would be painful.
Reminds me of my first few EV runs. We didn't bother with story mode. The rest of the group was (mostly) geared already, and at the time, I was the only smuggler. So for several runs, I would do my best until I died. On one occasion I remember dieing just as I got one last heal on the tank to down the droid boss.
Each week got better. Then they wanted to do EC, and the progression started all over in story mode. Only I was swapping toons based on who showed up. Healer/tank/rdps/mdps. Jack of all trades, master of none.
But now we've progressed to TFB hardmode and the twilek gunslinger modeled after Vette has evolved into my raiding toon. No more swapping. And my Skill as a DPS begins to fine-tune the way I learned to heal in EV. Learn the dance until you can do it with your eyes shut.