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I had the same question (although I did post it) just a few days ago when I went to the store. Right before I left my house I tried two programs, HandyShopper because it's freeware and the trial of ListPro. I ended up using ListPro 99% of the time because it was so much easier to use. However after comming home and being fustrated with HandyShopper I went online and read the manual. Once I new how to actually use HandyShopper I felt it was a better program (for shopping lists anyway).
The single most important feature of handy shopper is the abilty to have a your pre-made list, then while at the market you can enter the prices of each item and even add to the list. Handy Shopper will even calculate the total (including taxes) for you.
However for general lists I prefer ListPro because it has an easier layout and better looking user-interface.
P.S. Used it on my Dell Axim x51v A06
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