Line Item Separation in WooCommerce

I’ve been staring at the screen for a few minutes trying to figure out how to articulate this…

I am building a WooCommerce based site that contains solely custom paintings. The user purchases a canvas after choosing size and frame type, including specific creative direction and various options, and a few weeks later, a painting magically arrives on their doorstep.

I am using the Order Status setting in WooCommerce as a minimal type of project management to send the order through my colleagues at the office to efficiently complete each order. Each department will use the Orders area of WooCommerce to keep work flowing as it passes through departments. (ie: Sales < Operations < Artist/Purchasing < Framing Warehouse < Shipping < Accounting).

The Orders seem to flow great. But it only works right if each order contains ONE painting, and without a frame.

The trouble is two-fold:

1) ORDERS WILL OFTEN CONTAIN MULTIPLE PAINTING REQUESTS.
2) FRAMES ARE PURCHASED INSTANTLY THRU A VENDOR

In a nut shell, when someone orders a “24×18 Oil Painting of Attached Photo with Silver Frame) and a “46×30 Charcoal Drawing with Gold Frame”, I need to be able to divide the two items into 3 departments:

24×18 Oil Painting forwards to Artist A
46×30 Oil Charcoal Drawing forwards to Artist B
24×18 Silver Frame + 16×30 Gold Frame forward to Purchasing

I hope I am clear on what I am trying to do. I’m still wrapping my head around this, and I think I’m just heading down the wrong road.

I am open to using project management systems, but am not interested in a BaseCamp type thing. I want everything available to us in-house. And we can’t afford the monthly rate anyway right now. ??

Thank you in advance for your help!

[Moderator Note: No bumping. If it’s that urgent, consider hiring someone.]