Taking 20 is not about trying until you succeed, it is about trying over and over again until you get it right. Which essentially is trying until you do the best job you can.
It should be noted that a natural 1 on a skill check is not an automatic failure (almost that is - I think UMD has that condition) and a natural 20 is not an automatic success. In our games people have a habit of shouting out I rolled a natural 20 on my skill check, to which the DM almost always says "what was the result?".
Taking 20 also has an automatic "failure" associated with it. Even if you can't normally fail, even when rolling a "1" - you fail when taking 20. Remember that the player's aren't supposed to know the success number before hand. Even if the RAW has a "normal" number listed, the player does not know what (if any) circumstance modifiers are applicable.
Some skills specifically state you can't retry, and some don't say anything.
You can not take 20 on a hide check (ever) - because you have an automatic failure - and you can't attempt to hide if being observed (which is what the failure indicates on a hide check). It might be possible to take 10 on a hide check, depending on the circumstances and how the DM runs it - but you can't take 20 because of the automatic failure issue.
It should be noted that a natural 1 on a skill check is not an automatic failure (almost that is - I think UMD has that condition) and a natural 20 is not an automatic success. In our games people have a habit of shouting out I rolled a natural 20 on my skill check, to which the DM almost always says "what was the result?".
Taking 20 also has an automatic "failure" associated with it. Even if you can't normally fail, even when rolling a "1" - you fail when taking 20. Remember that the player's aren't supposed to know the success number before hand. Even if the RAW has a "normal" number listed, the player does not know what (if any) circumstance modifiers are applicable.
Some skills specifically state you can't retry, and some don't say anything.
You can not take 20 on a hide check (ever) - because you have an automatic failure - and you can't attempt to hide if being observed (which is what the failure indicates on a hide check). It might be possible to take 10 on a hide check, depending on the circumstances and how the DM runs it - but you can't take 20 because of the automatic failure issue.
