To help get over being scared to manage your computer, when you need to do something that you are unsure of, make a System Restore Point. That way if something does go awry, you can undo it. With the space that you have dedicated to backups, with the size of my C: partition, I could only keep two backups at a time, which may be sufficient, but I prefer more than that.
If you sending your file into the trash(recycle bin) then the drive D: maybe the main folder to store so you cannot do anything, it will not be empty the better idea is you can buy external drive and backup the files there and you can filter your data and again paste inside the folder or you can store your recyclebin into the C: it may help to manage.
thanks.