Do I have to enter a new description for every business expense? For example, if I had 50 business expenses can I lump them into one line item, or do I need to have 50?

Every expense of a type has to be entered separately. However, if you had 5 receipts for shipping for example, you could add them all together. The IRS wants to see how much you are spending and on what. They want to make sure a plumber is buying a wrench, not hairdressing supplies.