You’ll probably need some customization to tightly integrate this workflow, but below are a few recommendations.
Add-on extensions like Product Add-Ons or the more flexible Gravity Forms Product Add-ons can help to collect the various bits of info you need, including file uploads. You’ll also be able to adjust your prices to a certain degree of flexibility.
Alternatively, Measurement Price Calculator is an extension that you can configure to quote based on measurement. However, Product Add-ons is listed in the Partially incompatible section of its docs, so you’d have to experiment to find the limitations.
Your last request could be met through CRM extensions like WooCommerce Freshdesk that connects to an external helpdesk service, but links your customers and their orders with related communications.
If you have more specific questions about these extensions, feel free to ask them via this sales form.
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