second, this is a battle everyone and their mother (who stock trades) deals with. In the words of a famous man... greed is a mother fu*****!
....... Now on to my trading rules (keep in mind that you may want to scale these buys if you're trading less than 300-400 per options trade)
You're never 100% right. Sell 1/3 of your holdings @ 50% profit Sell 1/3 of your holdings @ 100% profit Sell 1/3 of your holdings at a logical trailing stop % based on recent movements. You're never 100% right.
As for your lessons.. I would edit them slightly :)
1) When dealing with "larger" positions option prices and profits/lossing swing greatly. Take profits and free ride
2) When you are upbig(REMOVE) SELL SOME. 1/2, 1/3, 1/4....