User file upload + chat feature plugins (with customer accounts)?

Hey all, 

I have a client who is after a website that can operate similar to something like Fiverr on a very small scale. He is a mix engineer and wants his clients to be able to chat to him via the website (to initially discuss orders) & upload files (potentially in the chat window). It also makes sense for customers to have accounts so they can see their chat history/ files they have uploaded).

Is this possible with Squarespace + plugins/ extensions?

Cheers!

This is not possible. nd even with other platforms, it is extremely complex and not easily accomplished with just 1-2 plugins.. You need to find another approach.