My statement is based on having used PD since 2011 and upgrading many times. Nobody can guarantee anything 100% regarding how software operates or interacts on a specific computer, and in my opinion it's far better to have a full c: drive/system backup than trying to manually choose every possible folder where PD hides things.
There are plenty of free and low cost options for making system backups, and I suggest that you spend some time figuring out which one works best for you. I also highly recommend that you make a backup and verify that you can restore it before you run into a situation where you have to do it, only to find out there's a problem. Once that's done, you can upgrade to DS without any worries.
The best part about having system images is that they will protect you no matter what happens to your PC - as long as you keep the backup(s) offline and possibly even offsite. Cloud storage and USD drives are both good optionschoices
The other thing is that you can mount the image as a virtual drive and simply copy any files or folders that you need without doing a full restore.
TL;DR Make a system backup before making any significant changes to your computer