I ran into trouble early on becase I was sick or out of town for much of the first few raid weeks (I'm STILL coughing) and missed out on most of the early wipe-a-thon trial by fire raids. I didn't even transfer right away because I didn't know what the raid schedule would look like. (what raid schedule? hah) So I had that same catch-22 issue right off the bat. But it gets exponentially worse the older content gets. This is why you have to hit the ground running at the start of any exp/tier. You wind up with competent raids only taking people with achievements and an ilevel higher than the fucking loot that drops, and everything else available is a sea of failure. Pugs only get worse over time, not better, which seems to defy logic. LFR hits and suddenly everyone thinks they are raid pros. Good players gravitate to the more experienced/geared groups and the latecomers are left with dogshit, no matter how good of a player they might think they are.
Sorrows, AOTC cheev may be gold but it won't get you past the ilvl filter unless you are making your own raids (and willing to herd the sheep.. ugh) And let me tell you, those sub 640 normal raids are fucking worthless, holy goddamn. First tectus mist? RAID EXPLOSION. I almost pooped myself laughing. 70% wipe for fuck's sake. I can't get my 636 rogue farther than 2/7. The raids are just that bad. I use 0 ilvl mod to check progress, and it's nothing but raid finder and 1/7 norms being led by some screaming try hard.
So yeah, the situation he describes - it only gets worse every week. And I knew this from experience, so that's why I hammered my balls to get those imp kills done. (and bitched about being left out because I knew it would only get harder every week)
tl;dr: If you think the Catch-22 is bad now, DON'T WAIT. Bust your balls now to save a lot of pain later.