Maintenance Tracking Excel Application/File

I am working on a volunteer project for a charitable organization to help track their maintenance activities and other activites that happen on a cyclical basis. This is a non-profit organization that is headed by people that are not "tech-savvy" so the excel file needs to be easy to utilize. I have somewhat of a barebones skeleton of the file and i have uploaded it here. In essence i need to have the maintenance data in the "Maintenance Data" tab be able to populate the calendar on the calendar tab till the end of the program date (December 2050). This mean if somebody enters a activity that happens weekly, it will populate according to its start date every week until December 2050. This is somewhat hard to explain bu should make sense when you look at the file. Other needs i need are as follows: On the "Calendar" tab, when you select the complete check box, you fill in your name and notes on the activity (notes only if necessary) and the information of the activity, the time that it was complete, who completed it, and notes on the activity (if necessary) will populate another tab so the information can be stored. If possible, the ability to upload a word/pdf file to associate with the activity that will act as a standard work.