questions about ecommerce

I'm wondering how much work I'm looking at, to implement the following:

• customer customizes product by entering a Name and Phone Number. (these need to be different from the actual customer billing/shipping info) So far, I've only seen select-list options
• customer uploads a file that is a list (xls, txt, csv, etc.) at checkout, or attached to the product they've selected.
• shipping rates tiered by quantity. (1-20 = $5.00, 21-30 = $6.00, etc.)

I've tinkered with ecommerce for a bit, going through the tutorial at drupalecommerce.org, but I haven't found ways to do these requested things yet. I would gratefully appreciate any tips you might have on how to implement these.

I'm using Drupal 5.3 and ecommerce 5.x-3.4. Would 4.0 alpha do better for me?