The limit is usually for printing the same label 5 times. Are you sure you purchased the label 5 times and did not try printing the same label 5 times. You can check this by going to the shipping labels page. The 5 labels should show up as individual purchases for each label as long as you are with in 24 hours of purchase there should be a reprint option. Also look at the labels you printed if the same label was printed more than once they will have the same tracking number.
If it turns out you did purchase 5 separate labels then perhaps this is a browser issue I would try a different browser.
Since this buyer bought 10 items through separate purchases you should be able to combine into 1 box and save on the cost of the shipping labels. After the label is purchased you would need to manually add the tracking to the other sales records. For multiple purchases with the same sales record number the tracking will automatically update for each item.
When combining shipping in situations were the buyer pays full price upfront I issue a partial refund for the difference in the cost of shipping to the buyer through PayPal. To get the difference I generally get the full shipping cost the buyer paid by looking at each order detail. Then I take 10 percent out for the final value fee on the shipping. Then when I purchase the label I subtract the cost of the label and the discount for purchasing online. The remaining amount I issue a partial refund through PayPal to the buyer.
