I started around wardrums and I definitely don't feel the plasticrack like I did for the first few sets I bought.
But as someone who did not start with harb I can totally see why there are so many repeats, I mean a beholder, one of the iconic dnd baddies who many many many dms would want and a fun DDM fig to boot is crazy expensive for a piece of plastic. (got one on a lucky draw, but another story). Point is, there is a demand for new kobolds and men in plate mail even if you have all you will ever need.
I think the upcoming set is kinda fugly, I am into the 4.0 rules but way not into their art direction. I have played the 2.0 DDM rules and I like them better than the old ones. Losing the use of my old figs (for a while) sucks but it is not like I used all of them for DDM anyway, more like 10% and with new new rule changes (assuming they don't make any major balance mistakes) it looks like more figures will be viable.
Anyway I will be doing what I have done for the last few sets, buy a case for a limited tourney with my DDM buddies and get singles of what I lack that is cool.