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I have no idea where to start. I want to create a widget. with the following features

  1. show a button to create a checklist.
  2. Show a list of already created checklists created by the user.
  3. Mark checklist as done.
  4. Send monthly report of the completed checklists.

Should I rather go with drupal or is this possible in wordpress?

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Each of those should be separate questions underlined with a rough concept: What is a checklist? User Meta? Post Type? What is a done checklist, etc. And each question will maybe have to get split into several other questions with specific tasks and code that you already tried that outlines a problem, shows where you're stuck, etc. – kaiser Dec 11 '12 at 8:19

Should I rather go with Drupal or is this possible in WordPress?

It is possible with WordPress. But also with Drupal. Or with Ruby on Rails. Or with Zend. Or with ... whatever programing language you can imagine.

I have no idea where to start. I want to create a widget.

WordPress has a dedicated Widgets API. And WP.SE has a dedicated that offers plenty examples.

with the following features

If you're expecting detailed code, then we're sorry, as this is forbidden according to our FAQ:

Note that we do not handle questions: that require professional hands-on involvement: overly complex and specific things (known as work for me for free)

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Thanks for the reply. I will try to form my questions better in the future. – sasdev Dec 13 '12 at 9:58

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