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I own both. And, I use both. (Not at the same time, but I alternate between Diary & PB/CB and also Pocket Plus and iLauncher.)
If you have and like Spb products like PP and Weather, Diary might make sense. It integrates weather forecast icons in the schedule shown on your today screen, which I think is a great feature. Also, Diary integrates your built-in notes (and also the Pocket Informant alarm notes which I use) as an included tab. It also has an included tab like CB. You can also run any of Diary's modules as a separate tab in Pocket Plus if you use that app. Diary must be installed to your main memory as of now.
In general, I think Diary is a little simpler than PB/CB.
Pocket Breeze/Contact Breeze has Amit, the developer. He's the best and most responsive developer that I've ever found. PB/CB have incredible customization options. You really can tweak it to your hearts content. And, it has a custom tab capability which allows you to run any other today screen plug-in as a tab within PB. That's awesome, and it's only going to get better when more custom tabs are permitted. In addition, if you use Pocket RSS as your newsreader, PB/CB already has a custom tab slot available for that app. I believe PB/CB will be including a notes component and better integration with the SBSH weather app: Pocket Weather in the future, but for now, it does not permit either of these in the same way that Diary already does.
In addition, PB/CB can be installed anywhere you want, and it will still run well and place the necessary elements in the main memory. As of now, there are all sorts of skins to customize PB/CB, too. Many for free.
Bottom line. I really like them both. Try them and see for yourself. But, I think Diary makes sense for someone who wants a simpler app and who uses other Spb products. PB/CB will work beautifully with Spb products, but is really one of the PPC enthusiasts essential apps.
Hope this helps a bit. It's certainly subjective, but I think it's helpful to hear from someone who uses both SBSH and Spb products and who like them both a lot.
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