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Yeah, I've done this too, with Ultralight S2S bags that have holed. Maybe I should see if they do their "big river" more durable version in 1L. I still don't like the roll top buckles closures that much but I guess they'd be waterproof at least (if new) unlike my plastic bag solution.
hippy-
mmm I get you - I've always just used the standard exped ones you can get in Millets, I use one for my camera in a stem bag too, that gets fairly beaten up as it comes out on every ride but no signs of damage yet. I tend not to bother with the roll top for tools/medical, I roll the entire thing round itself so its more space-efficient in a frame bag
jackbepablo
I use 1L dry bags for this sort of thing, though I'm not doing anything as gooch-destroying as you. For audax/touring I have two: one with medical-adjacent stuff in and one with tools that are additional to my normal ride tools