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I haven't watched indies in close to a decade, if anyone has any single show suggestions I'm all ears. I pretty much missed the british invasion but all those goes ended up being rapers so I don't feel so bad. But here are the must watches:
PWG, start with the first BOLA in late 05 and watch until Danielson vacates the championship.
ROH, start from the beginning, 2002 isn't all that great but it's an important transition in American indie wrestling. Where 3PW, CZW and XPW were trying to fill that ECW gap, ROH was not only being counter programming to them but also WWE. The code of honor was basically a kayfabe way of saying you weren't going to get a bunch of screwy finishes like you get on TV. You can stop watching in 09 when Jerry Lynn wins the title.
CZW, watch 05 (but maybe start with CoD 04). 05 was a perfect storm, Chikara had lost their training facility and briefly merged with the CZW school, this not only would pay off in the future with more well rounded trainees but in 05 it meant CZW had access to CHIKARAs guys. On top of that they were flying in PWG guys and Canadian guys. For 12 months they were THE super indie. After that you can check back in 09-2012. They had unique roster, and the most well rounded deathmatch wrestlers outside of Big Japan.
Chikara watch from 09-2011. The BDK is the best thing they ever did, maybe the most long term story in indie history. After that they got too far up their own asses, and before that the talent was too green.
But if you want something that's 100% worth your time, watch NOAH from it's founding until Go vs Saito. And before there are any accusations, I am cis gender and have had sex with my wife.