You talk about the importance of timing in regards to the market for buyers and sellers. I think it takes skill to make moves depending upon the market. For example, Kesler was planning on selling this season, saw there was just about no market for sellers this season, and instead realized it was a buyers market and bought a goalie to compete for a few more seasons.
I'd argue the salary cap is doing it's job perfectly, as Calgary, Quebec, Cologne, Davos, and Stockholm all have really good shots at a cup.
Also you're trade for a 3rd round pick either involves a part 2 or was really poor planning on your part.