Web Invoice—invoicing and billing for WordPress
By SH Mohanjith (http://mohanjith.com/)
Why it's awesome: Manage and send invoices directly from WordPress
Why it was picked: Easy to use, just enough power, subscription-based invoices

License: GNU General Public License
Manual Install URL: http://wordpress.org/extend/plugins/web-invoice/
Automatic Install search term: Web Invoice
Geek level: Newbie
Configuration location: Top Navigation | Products
Used in: Invoices
Web Invoice is an indispensable plugin for anyone who currently bills clients or offers any type of subscription service. Out of the box, Web Invoice supports one time payment invoices via PayPal.
To leverage Web Invoice's recurring billing feature, you will need to have either a PayPal Business or PayPal Payflow account. You can also leverage some other services such as MerchantPlus, MerchantExpress.com, or MerchantWarehouse. However, as I have never used these services, I can't reliably confirm if they work or not.

Web Invoice sends invoices via e-mail and includes a link that will redirect the client back to an online view of your invoice. Once the client reviews and approves the invoice, they can click the Pay Now link that will take them directly to PayPal.

Setting up an invoice
To create a new invoice, click New Invoice from the Web Invoice top-level navigation box within your WordPress administrator.
Select the client
Web Invoice uses your WordPress users as potential clients to bill by displaying all of the current users in a drop-down box. If your client is not present, simply click the "Create a new user account" link and complete the Add New User form.
Client Information
As WordPress does not collect address, company, and shipping information, you will need to complete the additional fields within the Client Information box. This step will only need to be performed once as Web Invoice will store this information next time you want to bill the same client.
Recurring Billing
In order to set up Recurrent Billing, you will need to click the "Create a recurring billing schedule for this invoice" link.
Subscription Name: This is the name of your subscription that will be displayed to the user when they are redirected to PayPal. For example, "Monthly Hosting" or eZine Monthly Subscription.
Start Date: You have the option of either starting the subscription immediately or starting it at a future date. To set a future date, you will need to click the Specify Start Date link and provide the specific starting date.
Bill Every: This field allows you to define how often this subscription will be billed. For example, you might provide 2 in the first input-box and select month(s) from the drop-down box in order to bill this client every two months.
Total Billing Cycles: You can choose how long this subscription service will be active by including the number of times to bill. For example, if you selected to bill every two months, and if you have six billing cycles, then your total subscription time will be 12 months.
Invoice Details
Subject: Provide a high-level overview of the purpose of this invoice. Additionally, the subject field will also be used as the main subject of the e-mail sent to your client.
Description/PO: Use the Description/PO field to offer more details about the invoice. The more detailed it is, the better.
Itemized List: Provide the name, description, quantity of items, and the unit price for each individual item. For example, Name: Monthly Hosting, Quantity: 1, Unit Price: $5.99.
Publish
Invoice ID: By default, Web Invoice will generate a unique Invoice ID, but you can set a custom one by clicking the "Custom Invoice ID" link.
Tax: Make sure you check with your State's tax requirements to know what Percentage (if any) is required for the types of items you are selling.
Currency: Change the dollar type required to pay.
Due Date: Determine when the invoice is due, you can subsequently pick from the clickable links for "In One Week" or "In 30 Days".