As its name suggests, Essentials does provide the basics: You can download transaction data from most banks and assign basic categories in order to track spending and income. You can also enter monthly bills and track which ones you've paid. And you can export data to tax preparation software that supports the .txf file format, including TaxCut and TurboTax. Microsoft's interface is pleasing, too, with its colorful spending pie chart and trackers that let you see whether you're adhering to spending limits that you specify for up to three categories of your choice.
But the account registers provide no field for notes to help you remember details of specific transactions (what concert did that Ticketmaster charge pay for?). And there's no support for transfer transactions: If you record a payment to Visa in your checking account, it won't show up in the register for that Visa account unless you enter it manually or download it from Visa. Furthermore, you can't divide a transaction between multiple categories. If you go shopping at Costco, for example, you can't assign part of the expense to groceries and part to clothing.
Not surprisingly, Essentials doesn't offer any of the investment and planning features that other versions of Money (to varying degrees) provide. For $20, I wouldn't expect it to.
But Microsoft hasn't revealed how much it will charge for online service support beyond the included year. People interested in desktop software might be better off investing in the $50 Deluxe version of Money (Microsoft offers a $20 mail-in rebate) and getting two years of support plus a tool they can grow into.
Both Microsoft and Intuit have done a good job of simplifying the new-user setup in their products to accommodate impatient customers. If you don't want to enter account data right away, simply skip to the home page. As a result of this improvement, there's less reason than ever to get a dumbed-down package.