Do it once, right, the first time. Your business email will be very important and a reliable resource for contact information. You may communicate with some clients using strictly email. With a basic support agreement you can get advice on what you need to upgrade. Maybe nothing, maybe just software.
It just takes the right setup for the situation. You should get a backup system setup too. That can be learning how to burn a DVD or could involve a hosted offsite backup solution with daily incremental backups. Call Scott eSolutions for an estimate on your eSolution or to find out more.