The userfiles folder

In CMSimple 4.x all folders for files, that are uploaded by the user, are subfolders of the folder "userfiles" in the CMSimple Root.

If you convert an existing page from an old CMSimple version, to CMSimple 4.0 or higher, you probably have a lot of images and downloads in the old folders "images/" and "downloads/" in the CMSimple Root.

In your content (content.htm) then these pictures, downloads and other files are appropriately linked or refered, and it would cause a lot of effort to change the links and image references in the content.htm.

My recommendation:

Simply let the old files (images, downloads etc.) in the old folders, so you have not to change the references in the old content.

But for new images and downloads use the new folders, and copy the old images to the new folder, if you want, so they are available for editor and filebrowser, to insert them to other places in the content.