I Cant figure how to make a Macro work

I am trying to condense over 50 pages of construction specs and pricing into a 1-2 page work order. Here is my thought process of how I think this should work, and I appreciate any advice/help i can get to help me with this. I have only about two more weeks to get this done.
I want to create a drop down box (I do know how to do this part) or a menu box (i have not figured this one out) with a list of items ex: Doors-Int, Doors-Ext, Windows, Insulation-Attic, Insulation-Wall.....
Once an item is selected, I want another "box" to come up with a list of values that corresponds to the specific item selected ex: if Window is selected... different sizes would be the next set of options to select from.. 3040, 4040, etc...
Once the size is selected, another "box" would allow the user to input a "quantity" in which once this is done, it would figure out the total amount of the line item and place in another cell along with the minimum specs required for the item. Once this is complete, I would need another "box" that would ask if there is another "Item" to be entered. If Yes, then the process would start over again on the next line below, and this process would repeat until the answer by the user is "no". Along with all of this, I would need the pricing to total out for the entire workorder at the bottom of the fianl page. Currently we do all this by hand (a lot of cut and paste) which consumes our time and ability to be productive. An Average work order is 8-12 pages long, just to give you an idea.

I am including a copy of a work order that we currently use. (Remember, we do most of this by cut and paste or by hand)

I hope I am not over stepping the boundries of what this forum is designed for, but tutorials alone are not helping me. I work for my local city, and to outsource this or to try and purchase a program, takes (to coin the phrase) "an act of congress" and way to much time.

Thanks again in advance for any help or guidance any of you may give.