Helping iTunes to help himself (and to hopefully lead a productive life)

Miscellaneous and Personal Stuff I Must Share
1

So. Imagine you’ve been buying albums… cassettes… CD’s… MP3s since high-school.

At some point you decided that the Rhapsody and Microsoft Music Manager sucked a bag of dicks and you fired both of them.
Your PC, “Brad” had a new friend called iTunes and they both swore up and down that he could do the job.

So you hired iTunes.

You brush the bugs out and add in the data on songs and albums (Thousands) over and over, getting everything right… like you are brushing the knots out of a kids hair after a camping trip.
Suddenly, your [del]car, which you named “Brad”[/del] PC crashes! WIN10 is corrupted and everything has to be reinstalled. Brad recovers… and sure the files are all there… so its simple right?

Not. Exactly.

“Brad”, you see has really bonded with iTunes … and iTunes is like that shitty drug-using friend who hangs around “Brad”, takes up space, and is Totally Fucking Useless at handling that ONE FUCKING JOB you hired him for (and is supposedly good at): finding, managing, and playing music.
Almost all of the links to the MP3s (thousands) are broken.

Now, you’re pissed… but iTunes isn’t yours (the license even says so) so you can’t just haul off and beat The Fear Of Compression into iTunes… as much as you’d like to.
Over time, you’ve given an awful lot of money to iTunes and if you beat the shit out of him and make him disappear, there is very little chance that you will ever get any of that money back.

So… much as it irks you to… you need to nurture and encourage iTunes (and hide from his sight the Unholy Wrath of The Fist Of Death)… but there is a problem.
iTunes isn’t as smart as “Brad” (… and if you didn’t know better, you’d swear his mother fucked a broken ATARI-2600…)

Yes, you COULD spend every day from now until February trying to fix every broken link in iTunes one at a time, like you are rubbing his damn nose in it, but that honestly feels like a waste of a Holiday Season…
Besides, other than the crash, Brad has been pretty good this year and you were hoping to get him some games.

So, hypothetically, what way would YOU use to help iTunes cope with this? Is there [del]a program[/del] an assistant you’d hire? One that will actually do the work?
(The last thing you need is for those two to be breeding and spawning all day long around “Brad”… and you know iTunes will if you don’t watch him like a hawk.)
You also don’t want to just throw money at iTunes. (…you just Fucking Know any money thrown at iTunes at this point will just be pissed away on drugs…)
Thoughts?
TL;DR …and you have less of a sense of humor than Trump with Hemorrhoids version:

How can iTunes be inspired to fix its own broken links to music / MP3s?

2

Did you keep backups? Just bring the latest library file (or whatever they call it in Windows).

If your iTunes shows the songs in the playlists, but shows broken links, it should find them on its own. you click on one, it says “should I look for it?” and you say yes, point it at the right directory, and it should ask “should I find all the other ones?” and you say yes, and in a few minutes all is well.

At least that’s how it worked for me when I screwed up my links.

3

Are all the mp3s in a single folder, with sub-folders for groups and albums?

If so, delete everything from iTunes (ETA: don’t delete the files, just delete them from iTunes) and then go to File>Add To Library and select the folder with all the mp3s in it.