Auto-populating a calendar based on two variables

All,
First off thanks for all the great ideas in the past. I thought I had some good ideas on how to do my current project, but I'm finding myself at a loss. I would like to be able to populate a calendar with training topics (I'm in the Navy) listed on a long range training plan (LRTP), encompassing the entire year. The problem is this LRTP is based on approved instruction so I have to keep the format of months, x's, etc. I would also like my Training Petty Officers to be able to select what days in a week their people conduct training. So in other words they populate the LRTP with X's under what month something is conducted and in no particular order, other than only occurring on previously selected training days, those items (training topic and number) get populated into the calendar, which is later approved by their leadership. Like I said, I had some good ideas, but now it seems impossible. Any ideas!?

Example posted. I used MS Office 2003. Thanks!Training PLan.xls

I had the thought today of utilizing MATCH and VLOOKUP along with RAND, but remembered that RAND changes every time you open the document. I'm racking my brain over this!!