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We have over 1,000 products in store. We are slowly adding to our website but would like the customers who are familiar with our products to be able to tell me what they want, and in turn, I create a quick invoice for them to sell them the product. ( need shipping and tax to be included as well ). is this even possible?

A simple form will do
Why wouldn’t you just put everything that’s for sale online?
Is woocommerce is not a good option? The new woocomemrce they move order table out of wp_post now. Take a look at it.
You can create an order inside of woocommerce itself adding any kind of amount, name it, add tax and shipping , customer data and send the invoice via mail.
You could create a form which the customer fills out „asking“ for product XY, with that data you could manually create an order, thus having all in one system. You could use something like wp automate too.