Do you have a router in the house? Most current internet "modems" are routers with multiple wired/wireless connection. If you do not have a router, get one. You now have 2 computers that need to be accessable from each other.
Create and share a folder on the new computer, and copy all of the Cakewalk folders to it.
Then copy those folders/files to the correct locations.
For presets: on the old computer, use the plugin manager to save all presets to a folder (c;\temp). Then copy the folder to the new computer and use the plugin manager to import all presets.
The projects do not need to be bundled.
You will have to install/register some of the third party plugins.
I would do a complete install of X1, and all updates. Then install X2, selecting all items in the list of plugs, synths,... And then the X2 updates. This way you will have all of X1's plugs and stuff. And can use X1 when a project does not open corrently in X2.
If you have 8.5, install it first.
And: you can install both 32 bit and 64 bit versions of all and every. if you have been using 32 bit sonar you may be using some 32 bit plugs that will not install with the 64 bit versions. Some of these will work in 64 bit, but they will not install via 64 intall.
DO NOT DELETE ANYTHING FROM THE OLD COMPUTER.
For grins, run the win8 upgrade advisor on the old comp. It may have a chip that will allow win8 to install. If so, you will have 2 similar computers. If not, it will run win 7.
In any case it can be used as a backup system via the network.
If no router, and in a hurry, use an external device: disk or usb stick. you can get the plugs, presets, and a few projects at a time this way. Cuz you do not have to have all the projects on the new comp to start playing.
Santa has been good to you.