You have clearly thought of some senario's that I have not thought of before myself. I now understand why so many other websites handle the shipping as a flat rate rather then a dynamic value. The obvious reason as to why I need to offer the live UPS shipping is that I stand to lose quite a bit of money per order if I settle on some arbitrary flat type of shipping price.
I do like the idea of charging for shipping per item only if a recurring charge is in the shopping cart. Because, as you have pointed out, a customer might order two different recurring payments like a weekly cricket order along with a monthly mealworm order. So, yes, I am in favor of doing this based on your recommendation as it seems to account for almost any possible customer purchasing senario. So, shall I do ahead and purchase the premium support ticket so you can get started tomorrow on this?