This was my concern too, it seems whoever's free agents auctions end early are going to get screwed, and whoever's drag on are going to win out. Simply put, it seems arbitrary who is going to do well in free agency, dependent upon which auctions are wrapped up early.
This is why I suggested when a GM wins an auction to retain their own player with bird rights, their new contract shouldn't immediately replace the cap hold. Rather, for the time being their cap hold would remain in place while the other auctions continue.
For example, I match bids on Jamal Crawford, whose auction ends before all other FA's. But rather than having to add his new $8m x 3 contract immediately to the books, putting me over the cap and therefore having to cancel or cease bidding in all the other still-live auctions, I carry on like before, only paying attention to how Jamal's $8m might effect my hard cap.
Or more simply, I reach an agreement with Jamal, sign the papers, but I don't hand them into the commisioner's office until I'm done pursuing other free agents.
Eradicating Marijuana one blunt at a time