Crypto Market #2 - Buying low to sell high or Buying high to sell higher

This is the age old trading question. Buy low and sell high or buy high and sell higher. With any investment where there is a possibility of loss you look at a chart to determine if it is a good time to buy. If the chart is going down when is the right time to buy and when the chart is going up we all know it has to come down some time, its the law of gravity right?

I personally do not like to buy into a position on the way down. I will usually wait until I see some sideways trading before I look to get in. Buying into a position on the way up seems a little better as the momentum is on your side. With that said I would rather wait for a pull back from the highs and some sideways trading before getting in.

Recently I have taken a different approach. I don't worry too much about the chart. I buy a small position and wait for the price action. When the price goes down I move it to the bottom of my list. If the price goes up I start looking to buy a little more. No one has ever made money on investments that go down. Keep that loser on your radar but don't double down when it drops like a knife. Move on to something that is working.

What do you think about this strategy?

Build positions in winners vs. pile in on a few names and hope for the best.