ArrowChat

Let the size of the biggest smiles, or the actual size of the smile to upload?

As big as you want. You'll have to change the width/height of the arrowchat_smiley class in the theme's CSS file.

any way to automatically size that?

You can set a size of all emoticons via CSS.

EXAMPLE
img.arrowchat_smiley {
height:20px;
width:20px;
max-height:100px;
max-width:100px;
}

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