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What keeps me from using obsidian (I’m sure this can be fixed but I’m lazy). The ideal handling imo is a pasted or web image url gets cached to an (owned) cloud url, though, i never thought through how to handle deletions. I guess file based in a cloud folder is good enough.

Yeah that's how dev.to does it! Tosses images on an AWS bucket. That would mean that... someone needs to own the hosting of course, which frightens me. Could be user configurable somehow?

when i was sketching this out for myself, thinking of how i'd make obsidian work like i wanted, I thought maybe i'd use a cloudinary api key because it handles all the conversion utility one might want for rando image urls