Bought more at key confidence building points, when it seemed to me that chance of survival, or even success, increased. For example, the non-collapse after the SR takedown and crucially for me, when the US decided to auction seized coins. This is rarely mentioned, but I think those auctions were a huge 'mistake' by TPTB. From their pov, they should have destroyed the coins - instead they literally legitimised BTC.
yeah once the silk road stack was auctioned by the government that was a big turning point. the government destroys seized evidence it considers illegal ie look at all the drugs destroyed by burning etc. by auctioning it i knew it was legit then.
dunno about you but back in the day when btc was a few bucks i threw it around like popcorn. just testing various wallets on different computers and to and from exchanges just to see how it worked. ive lost some coins by mistakes, some by forgetting about them. it was never a large percentage of course, but the amount ive lost would be worth a good amount today. but that was very early on when it was unknown if it would even survive.
if i had known what it would eventually be valued at i would of course been more careful, as i am now. back then in my wildest dreams i would never even of though it would hit 20k a coin. and i would of just laughed at anyone that said that. back in 2011-2012? pffft. coins were just things to play with.
EDIT: i mined my coins starting in 2011, didnt buy them. might be a reason i didnt value them much as i didnt pay money for them. just a byproduct of my gpus.