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The $.99 thing started just to psychologically cause people to think it is cheaper. At first glance, $99.99 looks cheaper than $100.00, when really what difference is a penny?

I've been wishing this would go away but, unfortunately, you're starting to see even $.98 and $.97 sigh

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This is exactly right. It's an old marketing trick, plays into your initial reaction with the price tag. And often times people will round it down instead of up, so $99.99 will be $99 dollars, saying "Man, I got this awesome painting for my wall, it was only $99" sounds more appealing than "Man, I got this awesome painting for my wall, it was only a hundred bucks".

Actually, it started as a bookkeeping method but I don't recall how it works. If a retailer added up all his sales at the end of the day, or during the transaction, it should always end in a certain way. Odd/even? Don't recall but that's the root of the idea.

It was because if something cost 9.99 and the customer gave a 10 dollar note, he would have to open the register to return a penny instead of pocketing the bill.

It's also the reason those cash registers made a loud ding when they opened.

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