Long story short, the nineteen teens Illinois pocket watch broke it's mainspring again.

The few local shops that still work on mechanical watches want $4-500 and a six month turnaround time to fix a watch that has no real value that isn't sentimental.

With that in mind, I'm debating buying a few watch tools and giving this a go myself.

Anyone work on their own watches?

No help here, but I’ve certainly thought about it. There are tons of watchmakers who post videos to YT that qualify as “how-to”, and the replacement parts and tools are accessible to the layman. I went so far as buying a chinesium automatic wristwatch from Amazon to disassemble and “study”, but I haven’t worked up the nerve yet.

Here's something that might be of interest (and help) to you -

https://www.youtube.com/@WristwatchRevival

He also sells watch repair tool kits for beginners.

I know there's a handful of watch tinkerers in the watch thread in the gallery.
Not sure if a pocketwatch is much different than wristwatches, but one of them could likely have some good input.

+1 for Marshall at Wristwatch Revival. He's the Bob Ross of watchmaking. I think you are on the right track in doing it yourself. Worst case is you have to send it for service.

Got another $600 quote today. Looks like it is probably me or nobody. My biggest question at the moment revolves around ensuring I'm getting the correct replacement spring.