My 2 bits
I bought during the last run-up, purchasing my last coins at 249. I believe it was that very evening that the crash happened.
Then I made the biggest mistake I've made so far. I got bummed out about the crash, lost some of my short term faith in bitcoin, and didn't see the resulting low prices as a buying opportunity. Instead, I slunk off to lick my wounds and pay down debt. I can't tell you how much I wish I had $2000 of that debt remaining, and $2000 worth of <100 coins.
With that said, I believe that every single person that didn't buy at <1 wishes they had bought them cheaper. I've decided to be happy that I bought any at all.
I didn't bought a <1 but I'm very happy about the price I bought in. Do you know why? Because I bought immediately after first reading about BTC, after a session of 24 hours reading about it non stop - so I got the best possible price considering when I first discovered BTC. Additionally, I increased my stash after the April crash, by both day trading a little and by buying more with fresh funds.
Four months later I first bought in, BTC was worth 20 times more; now it is worth 60 times more. Plus, I was very lucky with LTC, and MSC is doing quite well too. I don't know how I could wish anything different than I have. I don't know what you guys do for a living, but seeing an investment growing by 60-100 fold in one year is science fiction in the real world.