Item 1... Start with a recording to get the general workflow of the process. Go back after recording and massage/harden your NameMapping and functional timings to make for a re-runnable project.
Item 2... Read the documentation of on Property Checkpoints. This is the best way to do that kind of validation check. If you want to check the enable/disable before you proceeed on the workflow, a simple "if/then" logical flow on the property value will do that.
Item 3... This one is a bit more complex. It depends upon how the data is presented in order to determine how to extract it. I would steer away from a screenshot if possible...image comparisons are notoriously sensitive for slight differences. So, again, you could use the properties of the various objects for extracting the data. But, again, would depend upon how and where the data is presented.
For more specific, directed help with your specific application, we'll need screenshots of how the various parts show up in the Object Browser including all advanced property views.
Why automate? I do automated testing because there's only so much a human being can do and remain healthy. Sleep is a requirement. So, while people sleep, automation that I create does what I've described above in order to make sure that nothing gets past the final defense of the testing group. I love good food, good books, good friends, and good fun.