The following commentary is from an investment professional with Clear Harbor Asset Management who is a participant in TheStreet's expert contributor program.NEW YORK ( TheStreet) -- I've always been annoyed when I'm shopping for a product that is priced one penny below a flat dollar amount, like $19.99. Does the seller honestly believe I'm dumb enough to look at the price tag and think I'm paying any less than 20 bucks? Is it really a good idea to try and dupe your customer into thinking they're paying less than they really are with such a transparent ploy? Apparently, the answer is yes. Everywhere I go, I see this pricing strategy in action. Fly round-trip to Miami for just $49.99! Buy an iPad 2 for just $499.99! There is even a so-called "dollar store" chain called 99 Cents Only Stores ( NDN), which is really sticking it to higher-cost rivals like Dollar General ( DG) and Family Dollar ( FDO). Back in 2008, they announced raising their top price point for the first time in 26 years from 99 cents to 99.99 cents -- perhaps the most irritating move in the history of retail. Follow TheStreet on Twitter and become a fan on Facebook. This strategy could not be so widely employed if it annoyed everyone as much as it annoys me, or could it? Maybe there's a silent majority of consumers all over America who share my desire to see prices advertised more forthrightly. We'll find out soon thanks to JC Penney ( JCP).