adding to winners in long options has been a terrible strategy for me at least. I started doing this as a part of risk management, taking small 1-3% positions in several companies the met my criteria...if i was wrong and got wiped out not that big of a deal if i was right and the position went green I would add another 1%+. The vast majority of the time The underlying would move in my favor and in so doing IV increased...So I would buy the now overpriced contracts to add to my winner then It would either trade flat and IV crush+theta would eat me up or a small reversal would take place and my contract value would evaporate. Probably would work better when trading the underlying...And I have still lost less money adding to winners than i have via adding to losers...
Adding to winners is how I made my best ever trade, or bunch of trades. During a Dow uptrend I had a long position with a 2% capital risk. Entry to SL distance was ATR14. When the trade made 2% profit I added a second trade and moved the first trade's SL to its entry price. When the second trade made 2% I added a third trade and moved both earlier SL's to the second trade's entry price. And so on, multiple times. After a certain point, profit potential starts to rise exponentially and a capital loss is no longer a possibility. From that point on I increased the % capital risk on new trades, reaching 5%. Managed to bring in more than a year's salary in 3 weeks. Ah yes, the good old days.....