Calendar & Buttons

I am trying to create 2 completely separate spreadsheets for work and would like them to do a couple very specific things. Not even sure if it's possible, but it sounds like it would be.

1. I have a coversheet that has items on it for a customer. This is created by entering data on other worksheets in the same workbook so the cells need to stay put. Thing is, on this coversheet, it includes all of the customer's items. I want to be able to keep these items to use them when they order, but I want to hide the ones that I'm not currently using. Right now, I'm just manually hiding the ones I don't want to be printed out on the coversheet. Here's what I would like it to do; basically, when I open the document I would like for it to give me item buttons, buttons to click that indicate what I want hidden and want I want showing on the coversheet. That way, when I click OK after selecting the buttons of the items I want to be unhidden, they are the only ones that will print out. Is this possible?

2. This one I believe is a little easier. Basically I would like 12 monthly calendars as tabs, then another sheet for the data. The datasheet will have customers, a date, and a few other specifics. I like this datasheet primarily for reference, but the calendar is very necessary for routing trucks, when they'll be in certain towns, etc. Here's what I want; I want to be able to put the data into the datasheet, customer, city, profile number, date picked up, and quantity. I want this data, or some of it anyway, then referenced by the date onto the calendar in the correct day. I think a dropdown menu would be helpful for some of these things when inputting dates, but can't figure out how to make the datasheet "find" the correct date on the calendar, or vise versa.

Any advice to get this off the ground would be very useful and would simplify 2 very time consuming and monotonous tasks. Thank you.