Architectural Approaches to Upgrade
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There are two fundamental ways to upgrade Microsoft Windows SharePoint Services site definitions from Windows SharePoint Services 2.0 to Windows SharePoint Services 3.0: Either modify customizations in the previous version so that they function within the new version, or create a Windows SharePoint Services 3.0 site definition and subsequently upgrade the Windows SharePoint Services 2.0 definition.
To make your Windows SharePoint Services 2.0 site work with full functionality as soon as possible, you need an equivalent Windows SharePoint Services 3.0 site definition that matches your 2.0 site as closely as possible. You can either change a site definition that Windows SharePoint Services 3.0 installs, probably the site definition that's basically closest to your 2.0 site definition, or attempt to change your 2.0 definition so that it resembles a 3.0 site. Whether you choose the first or second approach depends on how much you have customized the 2.0 site definition. If you minimally customized the site definition (for example, merely added a new list type or added a few files), we recommend that you copy the equivalent 3.0 site definition and make the appropriate changes in it. Changing a 2.0 site definition to 3.0 is more difficult.
You must modify each page in your 2.0 site definition to make it compliant with Windows SharePoint Services 3.0. First of all, the page must contain an SPWebPartManager object, but in addition, you may need to remove some tags in the page to make it work. Also, you need to consider ways to make version 2 pages match the version 3 look and feel, as well as incorporate master pages.
After you put together a 3.0 equivalent, you can use an upgrade definition to map 2.0 files to 3.0 files. After you confirm that your upgrade works, you can begin the process of using build-to-build upgrade to map 3.0 upgraded sites to what you want, probably by using a lot of managed code to perform this fix-up.
The preferred approach to upgrading is to start with a Windows SharePoint Services 3.0 site definition and customize it to replace your 2.0 site definition. With this approach, you undertake an investigation of all the new 3.0 functionalities and attempt to incorporate these features as much as possible into your site (for example, use content types for lists, master pages for custom pages, and so on).
Test a new 3.0 site definition to determine whether it creates site instances and performs behaviors appropriately. If it does, the next step is to create an upgrade definition for moving sites from 2.0 to 3.0. Keep in mind that, if you choose to discontinue particular 2.0 site features, you may need to provide a 3.0 replacement. For example, even if you discontinue a particular custom list type, you may need to create list templates to support at least their upgrade.
We recommend that you start upgrade by using 3.0 site definitions, first design a 3.0 experience, and then use the upgrade process as a means to bring 2.0 customizations to the desired result in 3.0.