Shipping rules, quantities, per item

So thanks to the members here who I've spoken too and directed me to the Per Item and Per Quantity shipping extensions, it's really help alot with getting the idea of what i'm after almost there.

Unfortunately my client seems to have this more complex idea in his head and refuses to take any of the scenarios i've presented as plausible. What can I say, I work for him, since he pays me (and drives me insane ...rule #1 don't do work for family!!!)

So basically this is what's needed, he uses USPS to ship a number of items from CDs to TShirts. The CDs should almost always, unless put into a very large (unlikely) order be in a flat rate small box. TShirts on the other hand need to go into a FlatRate Small box for a quantity of 1-2, Med for 3-8, and Large for 8-15. During checkout, if someone orders say 3cds and 7Tshirts then he wants price to show that it's shipping in two separate boxes, a small for the CDs and a Med for the Tshirts. The Per-Quantity would work, but since there are two different items, he doesn't feel that it correctly shows what the packaging and pricing is going to be.

Is there any free/cheap shipping modules that could handle this type of need using USPS. If not USPS, one that's not associated with any postal service since really how it's shipped isn't going to change and as long as we can set the prices up to dynamically relate to his cost then it should matter.

An idea of a shipping module that I "envision" would be one that uses product categories and quantity based. So all CDs from ranges of 1-10 will be priced at a Small box, whereas all TShirt categories are priced for shipping with the details i posted above for small, med, and larges.

That's a pretty complex shipping set-up, and I'm fairly sure you're not going to find a shipping module that's going to do that for you. You could hire someone to write a custom one for you, but that's not going to be free/cheap.

I understand working with clients who won't take any of your suggestions, but I think the best solution in this case would be to tell him there's no other option. What would be the problem with using a standard shipping method (like weight-based, quantity-based, total-based, per item, etc.) where it charges the customer equal to or more than your client has to pay for shipping? It would be more of a "line of best fit" scenario than an exact equation for his shipping, but at least he wouldn't be losing money on shipping.

Yea, im going to try and come to a compromise with him. As the deadline is coming close before his stock gets fully setup and ready to go hes going to have to make a decision, hire a coder or take the solutions already prescribed. Keeping it cheap for both him and his clients should be his ultimate goal, so im just hoping whatever he chooses makes him happy with service with me (family gatherings would get awkward if not) lol.
Thanks johnathan for your response.