my I can't answer your first question. I don't "pin ". I always create desktop shortcuts.
RE : I also want to upgrade a Win 7 machine. Will my destop apps, shortcuts, and websites reappear in 10?
1. Your Win 7 has to have SP1 installed before you can get a free upgrade to Window 10.
2. Upgrade install will allow you to keep your files, settings and apps. Do NOT try clean install.
3. I created desktop shortcuts on my desktop and after upgraded to Win 10, there are still on my desktop. I upgraded windows 10 to my 2 laptops and shortcuts do not get deleted. Some might become inactive, such as Windows Update shortcut, and I would imagine that 3rd party programs that are not compatible with Win 10 would also become inactive.