I know people who have been reluctant to switch because they were afraid of having to go through the hands-on process of migrating their files.  Several ended up switching only after I volunteered to help them with the transfer.  In the past, Apple has promoted a third-party application called Move2Mac that helps users move files over to a Mac.  For those who want to move files on their own, Apple currently provides three generic ways users can transfer files over to a new Mac:

These methods require the user to manually perform the transfer.  It can be a tedious endeavor because the user must identify the files that he/she desires to move over to his/her Mac.  For example, the Direct connect and Network connection options require that the user, after successfully connecting to the Windows PC, open the Windows volume and drag and drop files over to the Mac.  The Alternative Methods require greater effort from the end user and include tasks such as burning files to CD or DVD and/or using a shared file server.

What if Apple made it easier to transfer files?  Apple wouldn’t have to promote third-party software and it could make the task so easy that even the most novice computer user could transfer their files.  I'd like to see an enhancement of the Direct Connect option or an alternative technology. Currently, the Direct Connect option uses an Ethernet cable to connect a Mac and a Windows PC.  The end user uses Finder to connect to their Windows computer by providing the PCs network address, PCs workgroup name, user name, password, and the volume (and folders) they wish to obtain files from.

Considering Apple's "Get A Mac" advertising campaign and efforts to get people to make the switch, I'd like to see an assistant in OS X 10.5 Leopard that streamlines the transfer process but intelligently scans the Windows computer for files such as documents, photos, email, etc.  The only thing the user needs to provide is the connection information to their old Windows system, the Windows Migration Assistant should handle the rest.

Apple states the following on page 12 in the Mac OS X Spotlight PDF (clicking the link will download the PDF):

Apple could easily develop software that could be installed on a Windows PC that would facilitate the transfer process.  What if Apple built a feature to extend Spotlight's indexing feature so that it could easily identify transferable files?  Currently, Spotlight works on drives formatted for Mac OS (HFS+ Mac OS Extended) but what if Apple was able to extend or leverage the technology for the purposes of transfers?  As an added bonus, the Migration Assistant should include an option that asks the user if they would like to import relevant files into the associated iLife application.  For example, mp3 files could be imported and organized into iTunes, photos could be imported and organized into iPhoto and so on.  The user could simply click a check box to enable the option and if left unchecked, files would be transferred only to the user's home directory into directories/folders such as Documents, Music, Pictures, and Movies.

The end result would be a simple, easy-to-use, organized process to help users easily transfer their files.  This would prove extremely useful for those not so savvy computer users.  Apple has the in-house expertise and capability to develop such an assistant/utility.  A Windows Migration Assistant would be a welcome addition to OS X Leopard. Apple could then promote the technology and demonstrate how easy it is to make the switch.