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You have to have one single recording of a run or in the case of an issue a recording of the transition between the two vods (so there is complete overlap)My recommendation would be to record locally at all times (and immediately delete if no PB and space is a concern), OBS can be set up to start recording when you go live, and then it is a non issue

I'd give it a shot, but it sounds better for the meme board imo

did you record the whole thing? can you just not upload it in one piece?

I would argue that ILs are an often ignored thing, and should be done cautiously, especially with a small community. I would say go easy, and find 2-3 hard to pull off levels to do and judge interest from there