Can't find the wish, so this might be the only one.

Found something similar though that you might be interested in: Adding Bulk Descriptions / Alt Text To Batch File Uploads AND Ability to Edit Such Descriptions On Any Previously Uploaded File

I know this has been discussed before, but it was probably pre-feedback site. In general I'd like to see better file management, especially when it comes to dealing with multiple files. For example, it's a major PITA¹ when you realize you should have resized those 30 images before uploading them. It's tedious to have to delete them one-by-one. If the bulk uploader allowed overwriting, it would be no big deal. With the way it is now, you end up with a duplicate set of files with the second set having the "(1)" appended to it.

It would be better if the original file was renamed so the new file could use the existing name. Then you could go back and delete the extra files at your leisure (unless you're using the image gallery). With the current setup, you would have to delete the original and then rename the corrected file you uploaded. Sometimes I find it easier to just completely delete the page and recreate it with the correct file set.

It would be better if the original file was renamed so the new file could use the existing name.

Actually, I disagree here. That is completely different behaviour to what the user would expect. The way it works now is the same as what the Windows OS does and is probably expected by most users.

Of course, Windows asks you if you want to overwrite the file as well, which Wikidot doesn't do for the multi-file uploader.

I agree that the last thing we need to do is confuse anyone more that than might be already! My point is that while the ability to upload lots of files in a batch is great, there are many features that are sorely missed once you realize you need to use them.

Yes, agreed.