@CraigBaker
I think the real problem is that you are most likely out of your depth. If you weren't you would know how to do this. The best thing would be to spend a few thousand (or hopefully less) getting conceptual help on what is feasible and practical, and then deciding whether your company wants to commit the time and expense to develop towards that solution. You don't necessarily have to do everything. You might find it very worthwhile cherry picking the easier parts initially and extending the project over a longer period.
@The_Doc_Man mentioned that it doesn't matter how big your company is, and that's a real issue. In general terms, a system needs to work just as well with one item as with 1000. It has to allow for all the special cases that arise. If 99% of the time you do one thing, but 1% of the time you do something differently, you have to allow for this 1% occasional event, or you will be stymied the first time the special situation arises.
You can't have a system that allows for, say, 3 alternatives, if once in a while you have more than 3 alternatives. What you need to do is develop a system that allows for multiple alternatives, however many that may be. This is really database thinking rather than spreadsheet thinking.
Good luck, anyway.