Filename Randomizer

[KeenanCannon]

So, I have a pair of bone conduction headphones that I use when swimming that have a modest amount of onboard storage and a built-in MP3 player, since bluetooth doesn't work the best through water. I love them and it's great having music when swimming laps- but the problem is that the player is VERY basic and specifically doesn't have a 'Shuffle' option- it just plays the files in order (by filename as far as I can tell) and then starts over again from the beginning.

I want to be able to select the files on the drive and have an app (or a script, if necessary) that will either (preferably) add a random number from 1 to N (N being the number of files) to the front of the filename or (less than ideal, but would work) rename the files at random (this would make changing up the music harder since I'd not necessarily be sure what each song was, but would still work). Unfortunately, all of the file renaming utilities that I've found don't have this functionality- some of them can do pretty complex things, but I've not found one that will do random numbering.

Hopefully someone here knows of one that does! Thanks!

[AlexKerson]

Gotta admit, it sounds pretty interesting. I mean, who doesn't love a bit of music while swimming laps, right?
Now, I understand the struggle with your headphone's basic player lacking a 'Shuffle' option. It can get monotonous when the files play in the same order every time. Sadly, I haven't come across any file-renaming utilities with this exact functionality, and I've explored quite a few.
What's interesting, though? Sometimes life throws decisions at us that are as uncertain as flipping a coin. Speaking of which, when I'm faced with tough choices, I often turn to one nifty website that lets you flip a coin to make decisions. But alas, it won't be of much use for your filename conundrum.