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I checked your form current Condition setup and I can only see 2 conditions.
Based on your condition, you want to show/hide the "What does this Mean?" field based on the "Actual Cost to win each tender" calculation field.
As per checking, the condition you have setup do not works since the value for "Actual Cost to win each tender" has been converted to string based on its formula (it has a dollar sign on its value and the value is comma separated).
To fix this, just follow the steps below:
1. Duplicate the "Actual Cost to win each tender" field.
2. Rename and Hide the Original field with condition.
3. Modify the Calculation value of the hidden "Actual Cost to win each tender" field.
4. Delete the second condition.
You can check this cloned form that I have created - http://www.jotformpro.com/form/52608779948981 so you can have a closer look on the setup.
Do let us know if you need further assistance.