I recommend a combination of paragraph styles, character styles and Find/Change, although Grep styles may also work, but I'm not all that familiar with them.
I'd set a basic body paragraph style, and use a character style to change the font for the check boxes. Depending on how the text is translated by the OCR process, use Find to get to the place where you want the checkbox, and replace it with the checkbox and what ever other text is necessary (spaces, tabs, etc.). Just be sure to click the More Options on the Find/Change window and set the Change Format to the character style.
1. Create a character style for your Wingdings
2. Add a GREP style to the paragraph style you are using for these lists. Have it apply thing Wingdings style to the GREP string
3. Then, for each of your list, select it and run this GREP Find/Change on your selection. Search for:
Will try! Txs. Will these also capitalize the first letter of the term (Arial capitalized)?
Another consideration is that usually the OCR doesn't recognize the checkbox but rather recognizes it as a "D" or "O". Usually I use a find/replace mechanism and do it very carefully as not to replace a proper "D" or "O".
Thank you very much!