From what I can recall from the dark time I still worked with Windows, you can copy over your desktop shortcuts (and whatever misc you put there), as well as the user folders like documents, pictures, etc.
I even did some funky stuff like copying over the user registry, but that got a bit funky here and there. Stuff like the start menu/screen configuration is also loaded in some retarded registry keys in binary format which are bound to the account they were made on, so you get to re-do those.
My last windows related project was actually to build a 'Microsoft Deployment Toolkit' setup, which can paste a pre-made windows image on a computer through a network boot and then make some scripted configuration changes and installations for more specific needs.
One glitch that came up there (and got one of my colleagues to basically rage-quit the project) was that when making your Windows image, if you made ANY modification to the windows apps or start menu/screen at all, any install done with that image would just plainly refuse to boot. This issue was born in 2012 along with Windows 8 and fairly widely reported, and was still around end of 2015 in Windows 10.
That wasn't the only issue this thing had either, there is a guide somewhere where during the install of your image-Windows you have to unplug the network cable at specific points to keep the thing from doing some stupid things which would again give you a useless dud of an image. The best part there is that you don't notice the image is borked until after you install the image build, run all 200-something updates (AAARGH), finished configuring it the way you want, then ran sysprep, packaged the whole install into an image, uploaded it to the deployment server and then ran the image on a test machine.
All in all it was still a fun project to work on, I got it working in the end and it was a huge improvement over 'intern with a Windows install disk' process. But god was that image building process a pain in the posterior.
I work with Linux now. Much less headache, can recommend to anyone.