Is the way wordpress handles media files a huge mess?

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I am currently in the process of weeding through massive amounts of thumbnails and regenerating thumbnails. Sometimes wordpress changes the original filename to scaled or appending -1 to the basename messing up the actual links to the images. I know webspace isn’t costly these days anymore, but with backups and especially once you have products on your website that need images this seems to explode.

I am somehow considering if picking wordpress was the right choice as my cms, as i don’t see a best practice down the road that might screw me up completely when it goes to backwards compatibility or changing thumbnails a few years from now.

Couldn’t the media handling be made a bit smarter and less prone to generating dead links in documents? Why is this such a mess?

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