First of all, if you are only going to file one tax return (your own), you probably won't save any money by switching to TurboTax Desktop. The way you save money is if you file multiple tax returns, say for yourself and several other family members. I will address your questions:
1. You can create tax data file in Online, and open it in Desktop. You won't lose any information, and won't have to re-enter any data. For instructions on how to make the switch see the following TurboTax Help Article: How do I switch from TurboTax CD/Download to TurboTax Online?
2. You have to purchase TurboTax Desktop each year. The software isn't "updated", it's a new program each year.
3. You can import 1099-DIVs and 1099-INT using any version of Desktop
4. Desktop comes with one free state, you can download others for a fee. Desktop also includes five free federal e-files, state e-filing is $20 (currently). The e-file process is pretty much the same as with Online.
Desktop has some features that I (being a CPA) think make it worth the cost, even if you only file a single return. Desktop has a "Forms" view where you can enter data directly on forms, schedules, and worksheets. You can see your return without having to print it. But you can't access your return from any device with an internet connection. It resides only on your hard drive.
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