How to have multiple input on the same field without using condition logic

For form https://form.jotform.com/61965885630973

Please look at field 39  - i am asking the user to put a check in each box if they want this information to be included.

If they do, then i give them the opportunity to update the text and date in two separate fields. And the date is by month or actual date. Using the conditional logic the way i could get it to work takes about 6 steps for each entry. Is there an easier way to do this that i am not seeing? there are many entries and other similar forms i am working and any time saving tips would help.

I think it will be simpler to use instead the Configurable List widget. 

link: https://widgets.jotform.com/widget/configurable_list

Here is a demo form with the widget on https://form.jotform.com/61654821574965

In your form https://www.jotformpro.com/form/61965885630973 you will need to add 12 Configurable list widget -- one for each the Checkbox option

The 1st column should be a static text (the descripiton similar to those in checkbox), then next column is Date and then 3rd is Textbox for the manual text/description input.

Hope this help. Let us know if you need further assistance.