Alright, I got my answers after a long night of research.
Not sure what actually sends PayPal the purchase info yet but I know why I don't get line item details.
If a customer uses a coupon or is part of a discount group, paypal does not get the itemized cart info. It just gets the total due.
if the customer does not have any discounts applied when checking out the cart shows all line items in all their glory.
Here is the line which verifies it.
$db->Execute("insert into " . TABLE_CONFIGURATION . " (configuration_title, configuration_key, configuration_value, configuration_description, configuration_group_id, sort_order, set_function, date_added) values ('Detailed Line Items in Cart', 'MODULE_PAYMENT_PAYPAL_DETAILED_CART', 'No', 'Do you want to give line-item details to PayPal? If set to True, line-item details will be shared with PayPal if no discounts apply and if tax and shipping are simple. Otherwise an Aggregate cart summary will be sent.', '6', '22', 'zen_cfg_select_option(array(\'No\',\'Yes\'), ', now())");
Hope that helps the next person that decides to give people discounts in their store.