How to do 300+ Check box's at once?

With Acrobat Pro this task should not take more than a minute, without using JavaScript or the detection wizard:

1. Create the first checkbox on the top left corner, set its "Export Value" to 1 (for example).

2. Right-clic upon this checkbox and use "Create Multiple Copies" to create the first column.

3. Select all checkboxes, copy-paste or ALT+clic&drag** to duplicate them as a second column, select all checkboxes of the 2nd column and set their "Export Value" to 2.

4. Select all checkboxes of any column, copy-paste or ALT+clic&drag** to duplicate them as a third column, select all checkboxes of the 3rd column and set their "Export Value" to 3.

5. Select all checkboxes of any column, copy-paste or ALT+clic&drag** to duplicate them as a fourth column, select all checkboxes of the 4th column and set their "Export Value" to 4.

6. And so on…

Since checkboxes on a row have the same name and a different "Export Value" they will act as radio-buttons.

If you need them to act as checkboxes (multi select), create the first row with 4 (or more) checkboxes with 4 different names, select all and use "Create Multiple Copies" to create columns.

** Add the Shift key to duplicate in a straight line

I don't have any tips on how to get the auto-detect to work better (maybe someone else does), but I would prepare a long form like that in InDesign and export as interactive PDF from InDesign. That way you wouldn't need to rely on auto-detect at all...

If the forms detection wizard doesn't work the options of doing it automatically are very limited.

One thing that does work is to use a script to create the check-boxes. That can be done if you use Wingdings to draw them in Excel.

If you do that then you could use this (paid-for) tool I've developed to create 100% accurate fields over those boxes, in a matter of seconds: Custom-made Adobe Scripts: Acrobat/Reader -- Convert Wingdings To Fields