I don't want to be glued to the market, all day, all the time. I do try to pay attention as to what's been going on.
I look at your first approach as a sunk cost trap. I've been guilty of it. I held a position in Nutrien for a long time. I was under water with it for most of the time I held it. With hindsight, I should have sold it not long after Russia invaded Ukraine. It spiked, and, greedy me, I thought it would stay there, so long as the war waged on. Finally several months ago, I sold it and moved on. It has gone nowhere since then. I can't imagine the tariff stuff is going to help them.
I purchased google a year after I retired, and have now owned it for 11years. The last several months have been disappointing, but the stock remains far above, what I have into it.
imo, a person does not have to try outsmart the market as much as just being in the market. Then you are betting on the economy generally, over a several year period. That has worked okay for me. I've been retired a dozen years and my retirement funds are half again larger than when I retired. We've lived a standard of living equivalent to when working, maybe a bit more.