Just been reading and will share my story if it makes anybody's story make more sense.
As you can see, WH member since 2004. Been to 26 DMB and 2 Dave solo shows. Most have been in CA, but I have also been to Cricket in Phoenix as well as some small shows in Europe when I lived there.
Other than the first year when I was denied my request, I have never been unsatisfied with my tickets. Second year, I had upper level arena seats and just before the lawn at the ampitheatre. I couldn't complain then because I knew I had no seniority.
Since then, I regularly get seats for near the front or middle of the midsection. Occasionally, I would say every fifth show, I get MUCH closer. Once had second row in 2006 through WH! IN 2009, I scored front row center at the Greek in LA! This year, I have pretty good seats for 3 of 4 shows (two of those shows are Atlanta and Charlotte and then Irvine in CA) and I have third row behind the pit for the fourth in Cula Vista, CA. So the region of the country I request for seems to have no effect on my ticket luck.
I never go through Middle Men. I roll the dice with WH. I pay the $30 partially so I don't have to deal with them. Would I like to be closer? Who wouldn't?
My personal experience leads me to believe that I consistently get "seniority" on a regular basis. This would mean all of the fans from the 90s and the beginning are still getting those lower seats in front of me. My usual seats are nearly always the same distance back and every fifth show or so, I get very lucky - which must be "random" shows. Just the pattern I've noticed.
I hope that the best seats don't go to the highest bidder. Part of the fun of being a loyal WH member is that I know I will get lucky every fifth show or so. It's those shows that are really special for me. Once scored a Carter drumstick from face value WH seats with 2004 seniority.