This is very true. I have also tried shorting couple of times and while I got lucky a few times, there were trades where my PUT options expired just a week befo

This is very true. I have also tried shorting couple of times and while I got lucky a few times, there were trades where my PUT options expired just a week before a big downturn. :D And they say "market is perfect" or something like that in the sense that everything is priced in. So if you wanted to short in already-bearish market, the implied volatility would make it cost-prohibitive. And if you would try shorting in "good times" where IV is low, often you would see bullish market and your option value just slowly decreasing to 0... It is always about timing and predicting the future, one way or another.