dates and auto populate data

I am trying to do a couple of things with these documents.  Both are Excel versions of paperwork that are filled out by hand. Both are weekly forms but get turned in monthly.  We have been having problems with staff not filling out the correct information i.e. dates and identifying information. I want to fill out as much as possible for them.  In the Weekly Notes file, I have been able to force it to do the dates but i wonder if there isn't a better way, plus with my way I have 10 pages (for 5 weeks) and if there are only 4 weeks in the month I would have an extra page printing for every instance (Person or Place).  So, here are my questions and/or request for how to do things.

1. Is there a better, more elegant way to make the days and dates auto populate. 
   1. Is there a way to just put in the month and have the first day of the month determined without needing to enter the date to begin the count from? (Like Weekly Notes file)
   2. Right now the Staff Daily Duties form has 2 pages that would cover the 1st week of the month.  Can it be configured to copy? the pages the correct amount of times for the whole month and fill for the number of weeks and stop at 4 or 5 weeks as needed.
2. I have been told that in order for the identifying info to be populated I would need to use mail merge.
   1. If I create a word version of these documents, can I pass the day and date info at the same time and the conditional formatting.  (Greying out dates not in the month)

I would appreciate any help with this.