The other idea I had was a dedicated wallet for people wanting to provide continuous pairings to darksend. Basically, it would be built off the existing wallet, but any coins sent to addresses in that client would automatically go through the darksend process 8 rounds. After anon'ing all the coins, the whole balance is automatically sent to a fresh address in the wallet where the process begins again. That way, there is always denominations out there for people to pair with. I don't know about you guys, but I would have no problem sending some DRK to a specialized wallet to help the network (at least as a intermediate step until I accumulate 1000 coin chunks to continue setting up masternodes). Logistics of the whole thing still to be determined.
Again, just ideas. Obviously I want the darksend process to be as easy as possible and to work when people want it to work.