I was looking at some service pricing for a company where this month they introduced a new promotion. The thing is, the promotion is exactly the same thing they offered last month except this offer was about 5% more expensive. While comparing it to the market in general still sounds like a great deal, seeing that it has been cheaper in the past just gave me a bias that one should wait until they see the company drop it to the lowest price.
I suppose that is one of the drawbacks of trying to be a savvy shopper as you often get fixated in wanting certain deals to return before you will make the plunge. I guess it is good for saving money, but at the same tie you could have been possibly depriving yourself of something that could have say increased your productivity which in a sense translates to more money and savings.
Usually I wait for about two months max to see if the deal will return or not if it is something that falls with that category. Unless the item is purely for entertainment, ten I can wait for as long as possible.