Skydiving is the only sport of which I know in which the more experienced one is, the more likely one is to hurt one's self. This holds true even when the numbers are normalized for total number of jumps. Put another way, on any given skydive, a jumper with one thousand jumps is statistically more likely to be seriously injured or killed than a jumper with only fifty.
The reasons for this are myriad. Veteran jumpers fly smaller, faster, more aerobatic canopies. They attempt more ambitious dive flows. They deploy at lower altitudes, fly canopies in formation* and perform aggressive hook-turn landings at high speed.
Simply, their level of experience allows them to attempt more dangerous things. This is fine, provided the level of danger does not exceed the level of experience and provided the jumper does not come to assume that they are invincible.
The number one killer of skydivers is operator error. For that matter, the number one killer of people is operator error. Whether it's things that can kill you instantly, like driving too fast, mixing recreational chemicals and, yes, skydiving or things that can kill you slowly, like smoking, overeating and a job you hate, if you ever want to have the wisdom of old age, you have to know your limitations.
*We call this Canopy Relative Work (CReW). It is arguably the most dangerous discipline in skydiving and it might be the most badass thing on Earth.