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However...
If you want to make it TRULY HACKABLE as you claim, you will not encumber it with cloud dependencies like you did last time. Let ME self host my own Pebble server if I choose. Go ahead and default to your servers and sell services and whatever, but let me host my own and switch the base URL to my own domain, preferably with open source software and simple APIs, without requiring me to go through your servers.
That way, even if this attempt also doesn't pan out, those of us willing to do the work will at least still have the functionality we want. I get the whole VC "lock them into required cloud services for life so we can make endless subscription revenue" model, but it's absolutely corrupt.
And, Eric, I know you know that - you have a hacker's heart. Please listen to it.
I wonder how practical it would be to add specific multidimensional similarity metrics the user could adjust. For example, if they didn't care whether it was a photo or drawing, but still had to be the same type of object. Or if they didn't care about the art style. Or if it had to be an SUV driving thru a river, but they don't care what colour SUV.
Perhaps some may be region locked out of downloading such resources which may be able to take you up on your offer though!