Chrome's code apparently stops adding a distinguishing number count to the filename after 100. To continue … show moresaving same-named files, you can manually increase the number count in the filename, but Chrome will not do it automatically. Alternatively, you can move the same-named files to a different folder, or change your download location in the Chrome settings.
Had an issue where I needed to constantly prompted to name the file before download and … show morethe file is not automatically saved with the correct extension. I had to manually edit the file afterwards and select the default program to open it. Upon checking the settings, you must enable the One-Click download so the prompt will be disabled. Hope this helps.