Ovinomancer
No flips for you!
As for your last graph about a playstyle where a player may have to choose "strategies" between how to advance quickly and how to "succeed more" when it comes to whether ot not to play his character in ways that fit his character traits or not... that is 1005 not what i would ever want to have happen in my games. That would be to me to be a fairly damning statement about a system. that certainly may be a fine set of "playstyle preferences" for your game or for other folks at other tables, but if i ever felt i put a system in place where "roleplaying your character" is at odds with "rate of advancement" or where "success at tasks in character" is at odds with "rate of advancement" i would feel as a GM that i had failed to deliver a reasonable system.
This would hit my "stupid rule" and die quickly.
i would feel incredibly stupid ever trying to tell a player that they should be weighing roleplaying vs success with rate of advancement hanging in the balance because that is the system i built/chose and what it was built/chosen to do.
others may not but hey, thats what it is.
Example: There are fourteen trolls in a lair, with a big pile of loot. This encounter is far above the expectation for success for the current group, but dice are dice so there's a chance. The best course for rapid advancement is to defeat the trolls and take their treasure. The best choice for the character is to not die trying to fight fourteen trolls because the odds of dying are very, very high. So, the best choice for continued success (to survive) is not the best choice for advancement.
This is an extreme example, but only because it highlights the constant tension even in 5e D&D between advancing quickly and succeeding more.