Your comparison of stock playing with marriage is sooper dooper relevant... and interesting!

Many people go into marriage as though they are into a sure thing... they don't want to 'miss the boat'...

But the underlying reality of the situation is that by the act of marrying, they only are only entering into an agreement to be together.

But this act alone certainly does not equate with marriage success.

In fact success in this context is made even more precarious and elusive.

For what one (or rather two) virtually did was bought a lottery ticket, as it were. Nothing more, nothing less.

The same principle applies with stocks...

I am sure you know what I mean...

Unless you can assure me the stock market will be in a bull run in the next few weeks or months...

Here is just my point of view. From what I have learnt in the past on proper way to short and comparing with your method, your method of shorting is a bit risky. In some way, you are guessing that you are at the peak. It is not always about getting the lowest price to buy and it is not always about getting the highest price to short. I would say your method of shorting would be more sucessful if based on candlestick i.e stock goes up to intra day high but ends up closing at below previous day closing price on a long down bar. The chances of shorting is higher.

So when you read people saying,"Oh I will wait till STI hit this level then I buy." These are the ones who will always end up "missing the boat". They are scared so they want "ideal price". Like marriage, maybe they want to marry the ideal partner in life. Sometimes it happens , but most fo the time no. 

What is the time frame?