What I ended up going with was a sidebar with the full list of items, and then in the content section of the page there's a list of the selected items with a type-ahead at the top which is connected to the sidebar list for the users who would rather type the items they want. I greyed out the selected items in the sidebar and the "Remove" button for each item ...
Here is a very well implemented multi select dropdown much like the one you mocked up. jQuery Rain | ParamQuery Select : jQuery Multi Select Plugin Features: ParamQuery select a.k.a. pqSelect is an open source jQuery select plugin that converts ordinary multiple and single select lists created with and HTML tags into theme ready jQueryUI widget with ...
You've mostly answered your own question, if you answer this one: Do your users need to upload images larger than 1MB? For reference, that's about 3 or 4 megapixel.
Both are valable, but it really depends on the goal you want to accomodate for. Always try and ask the 5 whys; this is what a "great startup" would probably do to. My technical respons would be that in this day and age its better to use the client side variant, as it lowers server load and presents more direct feedback. Client systems are more powerful as ...
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