Hi gtramble,
Having your invoices show information the way you want is a great way to save time and allow you to add your own creativity. I can help go over how to modify your invoice to show what you want.
In order to add dates to each line of your invoice you will need to modify the description on the Invoice page and manually add the dates. Once they are added they will show on the invoice in the description line when print it out.
Our developers are always looking to hear feedback about what businesses are looking for. If you want to have a report that shows a customer list by price level or the ability to customize to include it, you can submit ideas online by going to Help>Send Feedback Online>Product Suggestions.
Have a great night.