1) The idea for articles is that they effectively are permanent, that means we want to make sure the pictures in them don't up and disappear as the currents on the internet change.
Sure, you may be down for hosting your pictures for the next 10 years, but the same certainly can't be said for others and you never know for sure when someone's article pictures would then suddenly disappear.
In short, article pictures need to be hosted by us just for continuity sake (so no html tags in the wiki format).
2 & 3 are both great ideas (especially #3) but only legoburner can answer those questions for sure.
As of now, you can only upload one file at a time but if it is possible to implement, you can bet it is something we'll be doing.
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