Looks like you have shown me some light..though I have made a slight change in design, to me extracting data in the format I have mentioned for 1st screen will be bit difficult...any thoughts/suggestions are welcomed.
So instead of displaying plan for entire year, I decided to display current month with next and prev month buttons at top. This will be much easier to implement. Then using the tmpl_loop, as suggested above I will have to create a monthly calander with each holiday dates highlighted against all names. Any suggestions?