Even a mid-term bull trap could allow people to exit at 2x this price while you're waiting for sub-$1K prices. I prefer to wait for significant trading ranges to break, then ride the trend.
Yup. Even dumb ol' me knows that selling high is better. But you give no reason to suppose there will be any such major increase.
Again, any rise will run into exponential resistance as those now disenchanted sell out, when they get close to recovering their money. That's just an observation - my main point is that the overall trend will be down, meaning only the sharpest traders should buy along the way.