Are you just asking about having one tool tip with all the instruction in one balloon?
If you are , this is how I do a tool tip. Not sure this is what your asking for though..
While in DX Builder mode , right click on widget background, go to properties>Relation Tab > Cursor ( move cursor slider to ' hand' hit apply.
Then go to the Summary Tab...Click on Tool Tip Box. Type your instructions in tool tip box. Hit Apply and ok.
This will make your tool tip appear when cursor is placed anywhere near the entire background.
If you want the tool tip more localized then right click on an icon or any part of the object that has separate properties and do the same procedure.

Example:

Even when you make cursor be just ' hand' ? I never had that problem but I use small cursors. Im sure what your asking might be done through script but Im clueless on script.

When you open the tool tip box, before you add your tool tip, if you hit' enter' key on keyboard ( about 5 times or more depending on how far you want to go ) then type or paste in your tool tip it will space the tool tip down farther, not exactly what you wanted but its not blocked by cursor at least.

Those who script - script..and those who can't - fake it

So, basically instead of showing Thursday for today you want it to show the number 28?

That definitely requires a bit of tweaking within the script.

Edit: Depending on the Widget you should only have to change one thing to get the date number in text format. In the Aero Weather Widget if you go into the "weather_image" object change the following code: