Any way to handle this shipping methods

My clients shipping is very complicated and I gather she is able to do this on Etsy but has chosen to part ways with that company in favor of selling through her own site (the reasons not important). Here is the what I need and can I do it?

Each category has a different shipping rate (I see that this is not available but maybe someone will have an idea how this is accomplished)
Each country has a different shipping rate
Each additional item (from whatever category) is just .25 but the highest shipping rate is the main rate.

Example: Oranges ship at $5 Apples $2. The person buys 1 orange and two apples. Shipping would be $5 + $0.25 + $0.25 = $5.50. That would be to US. But to Canada shipping would cost $6 for oranges and $3 for apples and purchasing the same as above the total would be $6.50.

I know I can do zones for shipping to other countries but after that I'm a little stumped. The most important thing is the +$0.25 for each additional item, but I'd really like it if I can get the whole thing working.

PS: Just realized I posted this in the wrong section. My apologies