Greenhorn Question on Test Organisation

Hello,

I have been manually testing for years, new to automation/Test Complete.

1. We have a desktop application with dozens and dozens of menu options. How should I organize my testing?

For instance, should I create a folder for each menu item under KeywordTests and then build the tests for each menu item within those folders?

2. With some menus having quite a large number of negative test scenarios, should I first go through each menu item and build the positive tests? My thought there is that we would at least have the postive tests completed.

Thank you for your time, any suggestions on beginner videos or articles would also be appreciated.