Referencing, checkboxes, message boxes, using other workbooks

Hello,

I am creating a property checklist for my property inspectors to use that references other workbooks. Essentially it has basic yes and no questions that when answered populate a bid template - It is very difficult to put together with my caveman like skills at VBA and Excel.

On the back end, I have a database of prices per item and action for each item,
Headers are: item descriptions, action descriptions, quantity labels, room type... (Other fun stuff that I am still compiling on in a single work book)

I would like to develop this thing, so that my inspectors can walk through the property, tap yes and no answers on a questionaire, and fill out approx. area of damaged items. (Either pop-up boxes with answers that are populated on a sheet, a form, dropdown menues that when selected populate a predefined bid template, or checkboxes and buttons that help create the bid)

Things that I would like to happen while the the inspector is tapping and typing: (This model will assume using a laptop with windows 7)
I would like a folder to be created with the property address that the inspector inputs, as it's name, and the excel workbook to autosave in the folder.
I would like the answers that he selects to reference the items in my database that corelate to the question being asked... If it is a yes, I would like the item and action that he selects to reference the price in the database and populate fields in a bid template.
If the inspector's answer is a, "No," then I would like the space on the bid template to be used for the next item that is answered with a yes.
I would like to be able to email the excel workbook and/or pdf with the bid template to a set of email addresses. (Either pre-defined or an input box to define them)
I would like a separate workbook to track the property address, date, inspector, client, and amount of bid - So that I can run a report for my bosses.

What I need help with, is making this thing functional. Eventually I would like to host it on the web and allow other contractors in my industry the ability to use the program.

Any free advice, cheap advice, possible partners in creating a program that we can webhost and charge for, or any help at all would be greatly appreciated.

I greatly appreciate it,
ChrisHarrell
@CCCExteriors.com